Low-toxicity NMP substitute and method for preparing the same

Abstract

This invention provides a compound that can replace N-methylpyrrolidone (NMP), which is used in a variety of applications. [Solution] This technology relates to compounds of formulas I, II, III, and IV, as well as compositions containing one or more of these compounds, and methods for producing these compounds. The compounds of the present invention may be used as a substitute for NMP in a composition to produce a composition with lower toxicity. TIFF2026062912000082.tif42162

Description

[Technical Field]

[0001] Cross-reference of related applications This application claims the interests of U.S. Provisional Patent Application No. 62 / 976,469, filed on 14 February 2020, the entirety of which is incorporated herein by reference for all purposes. [Background technology]

[0002] background This technology generally relates to the field of N-methylpyrrolidone (NMP) substitutes. NMP, also known as N-methyl-2-pyrrolidone or 1-methyl-2-pyrrolidinone, is a colorless to yellowish liquid with a slight amine or "fishy" odor. NMP is used in a variety of applications, including paints or coatings, strippers, cleaners, adhesives / binders / sealants, leather treatments, personal care compositions, screen printing, pharmaceutical formulations, and manufacturing.

[0003] NMP is readily absorbed in humans and animals after inhalation, oral ingestion, and skin exposure. In experimental animals, NMP had low toxicity after short-term exposure to high levels via inhalation, transdermal exposure, and ingestion. However, when animals repeatedly ingested low levels of NMP, adverse effects included weight changes, liver weight changes, neurotoxicity, and thymic atrophy. Long-term oral exposure in animals also resulted in an increased incidence of renal enlargement, kidneys diagnosed with chronic problems, fluid in the pleural cavity, and testicular atrophy. In oral reproductive toxicity studies, NMP caused developmental toxicity, including decreased fetal weight and malformations. These effects were observed at doses lower than those causing maternal toxicity, indicating that maternal toxicity did not cause developmental toxicity.Additional information on the toxicity and health effects of NMP can be found in: U.S. Environmental Protection Agency, 2015, "TSCA Work Plan Chemical Risk Assessment. N-Methylpyrrolidone: Paint Stripper Use" (Non-Patent Literature 1); U.S. Environmental Protection Agency, 2017, "Scope of the Risk Evaluation for N-Methylpyrrolidone (2-Pyrrolidinone, 1-Methyl-)" (Non-Patent Literature 2); Administrative Agency for Chemical Safety and Pollution Prevention, EPA Document No. EPA-740-R1-7005 (Non-Patent Literature 3); Development (Non-Patent Literature 6); National Institute for Environmental Health (Netherlands), 2013, "Annex XV Restriction Report: Proposal for a Restriction. In RIVM, Bureau REACH", version 2, Netherlands: National Institute for Environmental Health (RIVM) (Non-Patent Literature 7), each of which is incorporated by reference.

[0004] Considering the toxicity associated with NMPs, alternatives to NMPs are needed. [Prior art documents] [Non-patent literature]

[0005] [Non-Patent Document 1] U.S. Environmental Protection Agency, 2015, "TSCA Work Plan Chemical Risk Assessment: N-Methylpyrrolidone: Paint Stripper Use" [Non-Patent Document 2] U.S. Environmental Protection Agency, 2017, "Scope of the Risk Evaluation for N-Methylpyrrolidone(2-Pyrrolidinone,1-Methyl-)" [Non-Patent Document 3] Office of Chemical Safety and Pollution Prevention, EPA Document Number EPA-740-R1-7005 [Non-Patent Document 4] .S. Environmental Protection Agency, 2018, "Problem Formulation of the Risk Evaluation for N-Methylpyrrolidone(2-Pyrrolidinone,1-Methyl-)" [Non-Patent Document 5] Office of Chemical Safety and Pollution Prevention, EPA Document Number EPA-740-R1-7015 [Non-Patent Document 6] Organisation for Economic Co-operation and Development, 2007, "SIDS Initial Assessment Report on 1-Methyl-2-pyrrolidone. Organization for Economic Cooperation and Development" [Non-Patent Document 7] National Institute for Environmental Health (RIVM), 2013, "Annex XV Restriction Report: Proposal for a Restriction. In RIVM, Bureau REACH," Version 2, Netherlands: National Institute for Environmental Health (RIVM) [Overview of the Initiative]

[0006] In one embodiment, the present technology provides compounds of formula I, formula II, formula III, or formula IV, In formula TIFF2026062912000001.tif42162, X is either O or CR. 33R 34 may also be, R 1 , R 8 , R 9 , R 17 , and R 26 may each independently be -CH3, -CH2CH3, -CH2CH2CH3, or -CH(CH3)2, R 2 , R 3 , R 10 , R 11 , R 14 , and R 15 may each independently be -H, -CH3, or -CH2CH3, R 6 and R 7 may each independently be absent, -H, -CH3, -CH2CH3, -CN 、 -C(O)N(CH3)2, -CH2C(O)N(CH3)2, -C(O)N(CH2CH3)2, -CH2C(O)N(CH2CH3)2, -CO2CH 3、または -CH2CO2CH3, R 16 is -O-C1-C8 alkyl, -O-C2-C8 (hetero)cycloalkyl, -O-C4-C 12 (hetero)aryl, -NH2, -NH-C1-C8 alkyl, -N(C1-C8 alkyl)2, TIFF2026062912000002.tif36165, R 18 and R 19 may each independently be -H or -C1-C8 alkyl, R 22 and R 23 may each independently be absent, -H or -C1-C8 alkyl, R 24 and R 25These are, independently, -H, -CN, -C1-C8 alkyl, -C2-C8 (hetero)cycloalkyl, -CH2-O-C1-C8 alkyl, -C(O)-C1-C8 alkyl, -C1-C8 alkyl -C(O)-C1-C8 alkyl, -C(O)-C2-C8 (hetero)cycloalkyl, -C1-C8 alkyl -C(O)-C2-C8 (hetero)cycloalkyl, -CO2H, -CO2-C1-C8 alkyl, -C1-C8 alkyl -CO2-C1-C8 alkyl, -CO2-C2-C8 (hetero)cycloalkyl, -C1-C8 Lukilen-CO2-C2-C8(hetero)cycloalkyl, -C1-C8alkylene-NH2, -C1-C8alkylene-NH-C1-C8alkyl, -C1-C8alkylene-N(C1-C8alkyl)2, -C(O)NH2, -C1-C8alkylene-C(O)NH2, -C(O)NH-C1-C8alkyl, -C(O)N(C1-C8alkyl)2, -C1-C8alkylene-C(O)NH-C1-C8alkyl, -C1-C8alkylene-C(O)N(C1-C8alkyl)2, -(hetero)aryl, -(hetero)cycloalkyl, It could also be TIFF2026062912000003.tif20133, R 4 , R 5 , R 12 , R 13 , R 20 , R 21 , R 31 , R 32 , R 33 , and R 34These are, independently, -H, -CN, -C1-C8 alkyl, -C2-C8 (hetero)cycloalkyl, -O-C1-C8 alkyl, -CH2-O-C1-C8 alkyl, -C(O)-C1-C8 alkyl, -C1-C8 alkyl -C(O)-C1-C8 alkyl, -C(O)-C3-C8 cycloalkyl, -C1-C8 alkyl -C(O)-C2-C8 (hetero)cycloalkyl, -CO2H, -CO2-C1-C8 alkyl, -C1-C8 alkyl -CO2-C1-C8 alkyl, -CO2-C2-C8 (hetero)cycloalkyl, -C1-C8 alkyl -CO2-C2-C 8(hetero)cycloalkyl, -NH2, -C1-C8alkylene-NH2, -NH-C1-C8alkyl, -N(C1-C8alkyl)2, -C1-C8alkylene-NH-C1-C8alkyl, -C1-C8alkylene-N(C1-C8alkyl)2, -C(O)NH2, -C1-C8alkylene-C(O)NH2, -C(O)NH-C1-C8alkyl, -C(O)N(C1-C8alkyl)2, -C1-C8alkylene-C(O)NH-C1-C8alkyl, -C1-C8alkylene-C(O)N(C1-C8alkyl)2, -(hetero)aryl, -(hetero)cycloalkyl, It could also be TIFF2026062912000004.tif58161, R 27 and R 28 These are, independently, -H or -Z-NR 35 R 36 It may be, and Z may be a C1-C8 alkyl, R 35 and R 36 Each of these may independently be -H, -C1-C8 alkyl, -(hetero)aryl, -(hetero)cycloalkyl, -C1-C8 alkylene-OH, -C1-C8 alkylene-NH2, -C1-C8 alkylene-NH-C1-C8 alkyl, or -C1-C8 alkylene-N-(C1-C8 alkyl)2, R 29 and R 30 Each of these may independently be absent, -H, -CH3, or -CH2CH3, and each of m, n, and p may independently be 0 or 1.

[0007] The present technology also provides a composition that may include a compound of Formula I, Formula II, Formula III, Formula IV, or a combination thereof. In any embodiment, the composition may be substantially free of NMP. In any embodiment, the compound may be used as an alternative (i.e., substitute) for NMP in the composition.

Mode for Carrying Out the Invention

[0008] Detailed Description As defined below, the following terms are used throughout:

[0009] As used in this specification and the appended claims, in the context in which an element is described (particularly, in the context of the following claims), the singular forms of the indefinite articles "a," "an," "the," and similar indicatives, etc., shall be construed to cover both the singular and plural, unless the specification states otherwise or the context clearly contradicts. The recitation of a range of values herein is merely intended to serve as a shorthand notation for referring individually to each separate value falling within the range, unless otherwise indicated herein, and each separate value is incorporated herein as if it were individually recited herein. All methods described herein can be performed in any suitable order, unless otherwise indicated herein or the context clearly contradicts. The use of any example, or exemplary language (e.g., "such as") provided herein is merely intended to better clarify the embodiments and is not intended to limit the claims unless otherwise stated. No language in this specification should be construed as indicating any non-claimed element as essential.

[0010] As used herein, "about" is understood by those skilled in the art and varies somewhat depending on the context in which it is used. When there is a use of a term not obvious to those skilled in the art, considering the context in which it is used, "about" means plus or minus 10% of that particular term.

[0011] Generally, "substituted" refers to an organic group (e.g., an alkyl group) as defined below in which one or more bonds to a hydrogen atom contained therein are replaced by bonds to non-hydrogen or non-carbon atoms. A substituted group also includes a group in which one or more bonds to a carbon atom or a hydrogen atom are replaced by bonds to a heteroatom including one or more double or triple bonds. Thus, unless otherwise specified, a substituted group is substituted with one or more substituents. In some embodiments, the substituent is substituted with 1, 2, 3, 4, 5, or 6 substituents. Examples of substituents include halogen (i.e., F, Cl, Br, and I); CF3; hydroxyl; alkoxy, alkenoxy, aryloxy, aralkyloxy, heterocyclyl, heterocyclylalkyl, heterocyclyloxy, and heterocyclylalkoxy groups; carbonyl (oxo); carboxylate; ester; ether; urethane; oxime; hydroxylamine; alkoxyamine; aralkoxyamine; thiol; sulfide; sulfoxide; sulfone; sulfonyl; pentafluorosulfanyl (i.e., SF5), sulfonamide; amine; N-oxide; hydrazine; hydrazide; hydrazone; azide; amide; amine; urea; amidine; guanidine; enamine; imide; isocyanate; isothiocyanate; cyanate; thiocyanate; imine; nitro group; nitrile (i.e., CN); and the like.

[0012] The term "leaving group" or "LG" refers to a group that can be easily substituted by a nucleophile such as an amine, alcohol, phosphorus, or thiol nucleophile, or their respective anions. Such leaving groups are well known and include carboxylate, N-hydroxysuccinimide, N-hydroxybenzotriazole, halogen (Cl - , Br - , and I -This includes halides (containing ), triflates, tosylates, mesylates, alkoxys, thioalkoxys, phosphinates, phosphonates, etc. Furthermore, the terms "leaving group" or "LG" mean to include leaving group precursors (i.e., moieties that can be readily converted to leaving groups by simple synthetic procedures such as alkylation, oxidation, or protonation). Such leaving group precursors and methods for converting them to leaving groups are well known to those skilled in the art.

[0013] Substituted ring groups, such as substituted cycloalkyl, aryl, heterocyclyl, and heteroaryl groups, also include rings and ring systems in which a bond to a hydrogen atom is replaced by a bond to a carbon atom. Therefore, substituted cycloalkyl, aryl, heterocyclyl, and heteroaryl groups may also be substituted.

[0014] The term "alkyl" refers to a group, whether alone or as part of another group (e.g., in dialkylamino), encompassing linear and branched aliphatic groups (i.e., saturated hydrocarbyl chains), and unless otherwise stated, having 1 to 10, 1 to 8, or 1 to 6 alkyl carbon atoms. Preferred alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, and hexyl. Unless otherwise stated, alkyl groups are optionally substituted with one, two, or three, preferably one or two, more preferably one substituent, which are compatible with the compounds, monomers, and polymers described herein. Typical substituted alkyl groups may be substituted one or more times with substituents such as those listed above, and are not limited to, haloalkyls (e.g., trifluoromethyl), hydroxyalkyls, thioalkyls, aminoalkyls, alkylaminoalkyls, dialkylaminoalkyls, alkoxyalkyls, and carboxyalkyls. In some embodiments, the alkyl group is unsubstituted.

[0015] Alkenyl groups include the linear and branched alkyl groups defined above, except that they have at least one double bond between two carbon atoms. Alkenyl groups have 2 to 12 carbon atoms, typically 2 to 10 carbon atoms, or in some embodiments 2 to 8, 2 to 6, or 2 to 4 carbon atoms. In some embodiments, alkenyl groups have 1, 2, or 3 carbon-carbon double bonds. Examples include, but are not limited to, vinyl, allyl, -CH=CH(CH3), -CH=C(CH3)2, -C(CH3)=CH2, -C(CH3)=CH(CH3), and -C(CH2CH3)=CH2. Typical substituted alkenyl groups may be monosubstituted or more than once, and may be monosubstituted, disubstituted, or trisubstituted with substituents such as, but are not limited to, those listed above.

[0016] The term "(hetero)cycloalkyl" refers to cycloalkyl and heterocycloalkyl groups.

[0017] The term "cycloalkyl" refers to a saturated cyclic hydrocarbon group. Unless otherwise specified, a cycloalkyl group has 3 to 12 ring carbon atoms, or 3 to 8 ring carbon atoms, or 3 to 6 ring carbon atoms. Preferred cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, and cyclohexyl. Unless otherwise specified, a cycloalkyl group is optionally substituted with 1, 2, or 3 alkyl groups, preferably 1 or 2, more preferably 1 alkyl group. In some embodiments, the alkyl group may contain 1 to 6 carbon atoms, preferably the alkyl group is unsubstituted and contains 1 to 4 carbon atoms. In some embodiments, the cycloalkyl group is unsubstituted.

[0018] As used herein, the term "heterocycloalkyl" refers to a non-aromatic ring compound having five or more ring members, at least three of which are carbon atoms and at least one of which is a nitrogen atom. In some embodiments, the heterocyclyl group contains one or two heteroatoms. In some embodiments, the heterocyclyl group may contain at least four or at least five carbon atoms. Typically, heterocycloalkyl groups are unsubstituted.

[0019] The term "(hetero)aryl" refers to aryl and heteroaryl groups.

[0020] Aryl groups are cyclic aromatic hydrocarbons that do not contain heteroatoms. Aryl groups as used herein include monocyclic, bicyclic, and tricyclic ring systems. Therefore, aryl groups include, but are not limited to, phenyl, azlenyl, heptarenyl, biphenyl, fluorenyl, phenantrenyl, anthracenyl, indenyl, indanyl, pentarenyl, and naphthyl groups. In some embodiments, the aryl group contains 6 to 14 carbon atoms, while in others, the ring portion of the group contains 6 to 12 or 6 to 10 carbon atoms. In some embodiments, the aryl group is phenyl or naphthyl. The term “aryl group” includes groups containing fused rings, such as fused aromatic-aliphatic ring systems (e.g., indanyl, tetrahydronaphthyl, etc.), but does not include aryl groups having other groups, such as alkyl or halo groups, bonded to one of the ring members. Rather, groups such as tolyls are called substituted aryl groups. Typical substituted aryl groups may be monosubstituted or more than once. For example, monosubstituted aryl groups include, but are not limited to, disubstituted, trisubstituted, quaternary, vposited, or hexasubstituted phenyl or naphthyl groups, which may be substituted with substituents such as those listed above.

[0021] A heteroaryl group is an aromatic ring compound containing five or more ring members, one or more of which are heteroatoms such as N, O, and S, but are not limited to these. Heteroaryl groups include, but are not limited to, pyrrolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridinyl, pyridadinyl, pyrimidinyl, pyrazinyl, thiophenyl, benzothiophenyl, furanil, benzofuranil, indolyl, azaindolyl (pyrrolopyridinyl), indazolyl, benzimidazolyl, imidazopyridinyl (azabenzimidazolyl), pyrazolopyridinyl, triazolopyridinyl, benzotriazolyl, benzoxazolyl, benzothiazolyl, benzothiadiazolyl, imidazopyridinyl, isoxazolopyridinyl, thianafthyl, purinyl, xanthinyl, adeninyl, guaninyl, quinolinyl, isoquinolinyl, tetrahydroquinolinyl, quinoxalinyl, and quinazolinyl groups. Heteroaryl groups include fused ring compounds in which all rings are aromatic, such as indolyl groups, and fused ring compounds in which only one ring is aromatic, such as 2,3-dihydroindolyl groups. The term "heteroaryl group" includes fused ring compounds but does not include heteroaryl groups that have another group bonded to one of the ring members, such as alkyl groups. Rather, heteroaryl groups with such substitutions are called "substituted heteroaryl groups." Typical substituted heteroaryl groups may be substituted one or more times with various substituents, such as those listed above.

[0022] An alkoxy group is a hydroxyl group (-OH) in which the bond to the hydrogen atom is replaced by a bond to the carbon atom of a substituted or unsubstituted alkyl group as defined above. Examples of linear alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy, butoxy, pentoxy, and hexoxy. Examples of branched alkoxy groups include, but are not limited to, isopropoxy, sec-butoxy, tert-butoxy, isopentoxy, and isohexoxy. Examples of cycloalkoxy groups include, but are not limited to, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, and cyclohexyloxy. Typical substituted alkoxy groups may be substituted one or more times with substituents such as those listed above.

[0023] As used herein, the terms “alkanoyl” and “alkanoyloxy” may refer to -C(O)-alkyl groups and -OC(O)-alkyl groups, respectively, that contain 2 to 5 carbon atoms. Similarly, “aryloyl” and “aryloyloxy” refer to -C(O)-aryl groups and -OC(O)-aryl groups.

[0024] The terms "aryloxy" and "arylalkoxy" refer to a substituted or unsubstituted aryl group bonded to an oxygen atom, and a substituted or unsubstituted aralkyl group bonded to an alkyl oxygen atom, respectively. Examples include, but are not limited to, phenoxy, naphthyloxy, and benzyloxy. Typical substituted aryloxy and arylalkoxy groups may be substituted one or more times with substituents such as those listed above.

[0025] As used herein, the term "carboxylate" refers to a COOH group or its ionized form, -COO - It refers to.

[0026] The term "ester" as used herein refers to -COOR 70 And refers to the -C(O)OG group. 70is a substituted or unsubstituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, aralkyl, heterocyclylalkyl, or heterocyclyl group as defined herein. G is a carboxylate protecting group. Carboxylate protecting groups are well known to those skilled in the art. A comprehensive list of carboxylate functional protecting groups that can be added or removed using the procedures described herein can be found in Protective Groups in Organic Synthesis, Greene, TW, Wuts, PGM, John Wiley & Sons, New York, NY, (3rd edition, 1999), to the same extent as is fully described herein, and is incorporated herein by reference in its entirety for all purposes.

[0027] The term "amide" (or "amido") refers to C- and N-amide groups, i.e., -C(O)NR, respectively. 71 R 72 and -NR 71 C(O)R 72 It contains the group R 71 and R 72 This is independently hydrogen, or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, heterocyclylalkyl, or heterocyclyl group as defined herein. Thus, the amide group includes, but is not limited to, a carbamoyl group (-C(O)NH2) and a formamide group (-NHC(O)H). In some embodiments, the amide is -NR 71 C(O)-(C 1-5 The alkyl group is called "carbonylamino," while the amide group is -NHC(O)-alkyl, and the group is called "alkanoylamino."

[0028] As used herein, the terms "nitrile" or "cyano" refer to the -CN group.

[0029] The urethane group contains N- and O-urethane groups, i.e., -NR, respectively. 73C(O)OR 74 and -OC(O)NR 73 R 74 groups are included. R 73 and R 74 are, independently, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, heterocyclylalkyl, or heterocyclyl group as defined herein. R 73 may be H.

[0030] As used herein, the term "amine" (or "amino") refers to a -NR 75 R 76 group, where R 75 and R 76 are, independently, hydrogen, or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, heterocyclylalkyl or heterocyclyl group as defined herein. In some embodiments, the amine is alkylamino, dialkylamino, arylamino, or alkylarylamino. In other embodiments, the amine is NH2, methylamino, dimethylamino, ethylamino, diethylamino, propylamino, isopropylamino, phenylamino, or benzylamino.

[0031] The term "urea" refers to a -NR 84 -C(O)-NR 85 R 86 group. The R 84 , R 85 , and R 86 groups are, independently, hydrogen, or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, heterocyclyl or heterocyclylalkyl group as defined herein.

[0032] As used herein, the term "halogen" or "halo" refers to bromine, chlorine, fluorine, or iodine. In some embodiments, the halogen is fluorine. In other embodiments, the halogen is chlorine or bromine.

[0033] As used herein, the term "hydroxyl" refers to -OH or its ionized form, -O - This can refer to the following. The "hydroxyalkyl" group is a hydroxyl-substituted alkyl group such as HO-CH2-.

[0034] The term "imide" is -C(O)NR 98 C(O)R 99 It refers to R 98 and R 99 Each of these is independently hydrogen, or a substituted or unsubstituted alkyl, cycloalkyl, alkenyl, alkynyl, arylaralkyl, heterocyclyl, or heterocyclylalkyl group as defined herein.

[0035] The term "imin" is -CR 100 (NR 101 ) and -N(CR 100 R 101 ) refers to the base, R 100 and R 101 Each is independently hydrogen, or a substituted or unsubstituted alkyl, cycloalkyl, alkenyl, alkynyl, arylaralkyl, heterocyclyl or heterocyclylalkyl as defined herein, except R 100 and R 101 Neither of them is hydrogen at the same time.

[0036] As used herein, the term "nitro" refers to the -NO2 group.

[0037] The term "acrylate reagent" refers to formula R 102 This refers to a reagent having a C(O)- group, where R is in the formula. 102 is a substituted or unsubstituted alkenyl group as defined herein. Typical acrylate reagents include H2C=CHC(O)-, H2C=C(CH3)C(O)-, H2C=C(CH2CH3)C(O)-, H3CCH=CHC(O)-, (H3C)2C=CHC(O)-, (H3C)2C=C(CH3)C(O)-, etc. In some embodiments, the acrylate reagent is of formula R102 may also refer to C(O)-LG, where LG is a leaving group as defined herein. Non-limiting examples of acrylate reagents include acryloyl chloride, methacryloyl chloride, acryloyl tosylate, methacryloyl tosylate, acryloyl mesylate, methacryloyl mesylate, acryloyl -O-alkyl, methacryloyl -O-alkyl, and the like. In some embodiments, the acrylate reagent is R 102 C(O)-OR 103 、R 102 C(O)-NR 104 R 105 and may also refer to, where -OR 103 and -NR 104 R 105 do not detach, and R 103 、R 104 、R 105 are independently hydrogen or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, heterocyclyl, or heterocyclylalkyl group as defined herein.

[0038] The term "alkanoyl reagent" refers to the product formed by nucleophilic Michael addition to an acrylic acid reagent. Representative alkanoyl reagents include H2C(Nuc)CH2C(O)-, H2C(Nuc)CH(CH3)C(O)-, H2C(Nuc)CH(CH2CH3)C(O)-, H3CCH(Nuc)CH2C(O)-, (H3C)2C(Nuc)CH2C(O)-, (H3C)2C(Nuc)CH(CH3)C(O)-, etc., where Nuc is a nucleophile. In some embodiments, the nucleophile may be a nitroalkane.

[0039] Groups described herein that have two or more bonding sites (i.e., divalent, trivalent, or polyvalent) within the compounds of this technology are indicated by the use of the suffix "ene". For example, a divalent alkyl group is an alkylene group, and a divalent cycloalkyl group is a cycloalkylene group, and so on. Substituents having a single bonding site to the compounds of this technology are not referred to using the designation "ene". Therefore, for example, chloroethyl is not referred to as chloroethylene herein.

[0040] As used herein, “substantially absent” refers to a specific component in less than about 2% by weight, based on the total weight of the composition. In some embodiments, the composition may contain less than about 1% by weight, less than about 0.5% by weight, or less than about 0.1% by weight. In some embodiments, the composition may not contain substantially any NMP. In some embodiments, the composition may not contain any detectable amount of any component. For example, in any embodiment, the composition may not contain any detectable amount of NMP.

[0041] As will be understood by those skilled in the art, for all purposes, and especially in terms of providing written explanations, all scopes disclosed herein also encompass all possible subscopes and combinations thereof. Any scope listed is well described and readily recognizable as being able to be decomposed into at least equal halves, thirds, quarters, fifths, tenths, etc. As a non-limiting example, each scope described herein can readily be decomposed into lower thirds, middle thirds, upper thirds, etc. As will be understood by those skilled in the art, all words such as “maximum,” “at least,” “greater than,” and “less than” include the listed numbers and refer to scopes that can subsequently be decomposed into subscopes as described above. Finally, as will be understood by those skilled in the art, a scope includes each individual member. Thus, for example, the group having 1 to 3 atoms refers to the group having 1, 2, or 3 atoms. Similarly, the group having 1 to 5 atoms refers to the group having 1, 2, 3, 4, or 5 atoms, and so on.

[0042] Those skilled in the art will understand that the compounds of this art may exhibit tautomerism, conformational isomerism, geometric isomerism, and / or stereoisomerism. Since the drawings of the formulas in this specification and the claims can only represent one of the possible tautomers, conformational isomers, stereochemicals, or geometric isomers, it should be understood that this art encompasses all tautomers, conformational isomers, stereochemicals, and / or geometric isomers of compounds having one or more of the uses described herein, as well as mixtures of these in various different forms.

[0043] "Tautomers" refer to isomers of a compound that are in equilibrium with each other. The presence and concentration of isomers depend on the environment in which the compound is found, for example, whether the compound is a solid or in an organic solution or aqueous solution. For example, in aqueous solution, guanidine may exhibit the following isomers in protic organic solutions, which are also called tautomers.

[0044] Due to the limitations of representing compounds using structural formulas, please understand that all chemical formulas of the compounds described herein represent all tautomers of the compound and are within the scope of this technology.

[0045] In one embodiment, the present technology provides compounds of formula I, formula II, formula III, or formula IV, In formula TIFF2026062912000005.tif44160, X is O or CR 33 R 34 It may be R 1 , R 8 , R 9 , R 17 , and R 26 Each of these may independently be -CH3, -CH2CH3, -CH2CH2CH3, or -CH(CH3)2, R 2 , R 3 , R 10 , R 11 , R 14 , and R 15Each of these may independently be -H, -CH3, or -CH2CH3, and R 6 and R 7 These are, independently, absent, -H, -CH3, -CH2CH3, and -CN. 、 -C(O)N(CH3)2, -CH2C(O)N(CH3)2, -C(O)N(CH2CH3)2, -CH2C(O)N(CH2CH3)2, -CO2CH3, or -CH2CO2CH3, R 16 These are -O-C1-C8 alkyl, -O-C2-C8 (hetero)cycloalkyl, and -O-C4-C 12 (hetero)aryl, -NH2, -NH-C1-C8 alkyl, -N(C1-C8 alkyl)2, It could also be TIFF2026062912000006.tif46140, R 18 and R 19 Each of these may independently be -H or -C1-C8 alkyl, and R 22 and R 23 Each of these may independently be absent, -H, or -C1-C8 alkyl, and R 24 and R 25These are, independently, -H, -CN, -C1-C8 alkyl, -C2-C8 (hetero)cycloalkyl, -CH2-O-C1-C8 alkyl, -C(O)-C1-C8 alkyl, -C1-C8 alkyl -C(O)-C1-C8 alkyl, -C(O)-C2-C8 (hetero)cycloalkyl, -C1-C8 alkyl -C(O)-C2-C8 (hetero)cycloalkyl, -CO2H, -CO2-C1-C8 alkyl, -C1-C8 alkyl -CO2-C1-C8 alkyl, -CO2-C2-C8 (hetero)cycloalkyl, -C1-C8 Lukilen-CO2-C2-C8(hetero)cycloalkyl, -C1-C8alkylene-NH2, -C1-C8alkylene-NH-C1-C8alkyl, -C1-C8alkylene-N(C1-C8alkyl)2, -C(O)NH2, -C1-C8alkylene-C(O)NH2, -C(O)NH-C1-C8alkyl, -C(O)N(C1-C8alkyl)2, -C1-C8alkylene-C(O)NH-C1-C8alkyl, -C1-C8alkylene-C(O)N(C1-C8alkyl)2, -(hetero)aryl, -(hetero)cycloalkyl, It could also be TIFF2026062912000007.tif20132, R 4 , R 5 , R 12 , R 13 , R 20 , R 21 , R 31 , R 32 , R 33 , and R 34These are, independently, -H, -CN, -C1-C8 alkyl, -C2-C8 (hetero)cycloalkyl, -O-C1-C8 alkyl, -CH2-O-C1-C8 alkyl, -C(O)-C1-C8 alkyl, -C1-C8 alkyl -C(O)-C1-C8 alkyl, -C(O)-C3-C8 cycloalkyl, -C1-C8 alkyl -C(O)-C2-C8 (hetero)cycloalkyl, -CO2H, -CO2-C1-C8 alkyl, -C1-C8 alkyl -CO2-C1-C8 alkyl, -CO2-C2-C8 (hetero)cycloalkyl, -C1-C8 alkyl -CO2-C2-C 8(hetero)cycloalkyl, -NH2, -C1-C8alkylene-NH2, -NH-C1-C8alkyl, -N(C1-C8alkyl)2, -C1-C8alkylene-NH-C1-C8alkyl, -C1-C8alkylene-N(C1-C8alkyl)2, -C(O)NH2, -C1-C8alkylene-C(O)NH2, -C(O)NH-C1-C8alkyl, -C(O)N(C1-C8alkyl)2, -C1-C8alkylene-C(O)NH-C1-C8alkyl, -C1-C8alkylene-C(O)N(C1-C8alkyl)2, -(hetero)aryl, -(hetero)cycloalkyl, It could also be TIFF2026062912000008.tif59161, R 27 and R 28 These are, independently, -H or -Z-NR 35 R 36 It may be R 29 and R 30 Each of these may independently be absent, -H, -CH3, or -CH2CH3, and each of m, n, and p may independently be 0 or 1. In any embodiment, Z may be a C1-C8 alkylene, and R 35 and R 36 Each of these may independently be -H, -C1-C8 alkyl, -(hetero)aryl, -(hetero)cycloalkyl, -C1-C8 alkylene-OH, -C1-C8 alkylene-NH2, -C1-C8 alkylene-NH-C1-C8 alkyl, or -C1-C8 alkylene-N-(C1-C8 alkyl)2.

[0046] In some embodiments, R 1 R may be -CH3. In some embodiments, 1 R may be -CH2CH3. In some embodiments, 1 R may be -CH2CH2CH3. In some embodiments, 1 This could also be -CH(CH3)2.

[0047] In some embodiments, R 8 R may be -CH3. In some embodiments, 8 R may be -CH2CH3. In some embodiments, 8 R may be -CH2CH2CH3. In some embodiments, 8 This could also be -CH(CH3)2.

[0048] In some embodiments, R 9 R may be -CH3. In some embodiments, 9 R may be -CH2CH3. In some embodiments, 9 R may be -CH2CH2CH3. In some embodiments, 9 This could also be -CH(CH3)2.

[0049] In some embodiments, R 17 R may be -CH3. In some embodiments, 17 R may be -CH2CH3. In some embodiments, 17 R may be -CH2CH2CH3. In some embodiments, 17 This could also be -CH(CH3)2.

[0050] In some embodiments, R 26 R may be -CH3. In some embodiments, 26 R may be -CH2CH3. In some embodiments, 26R may be -CH2CH2CH3. In some embodiments, 26 This could also be -CH(CH3)2.

[0051] In some embodiments, R 2 It may be -H. In some embodiments, R 2 R may be -CH3. In some embodiments, 2 -CH2CH3 may also be used.

[0052] In some embodiments, R 3 It may be -H. In some embodiments, R 3 R may be -CH3. In some embodiments, 3 -CH2CH3 may also be used.

[0053] In a particular embodiment, R 2 and R 3 Together, they may contain at least one carbon atom. In certain embodiments, R 2 and R 3 These together may contain at least two carbon atoms.

[0054] In some embodiments, R 10 It may be -H. In some embodiments, R 10 R may be -CH3. In some embodiments, 10 -CH2CH3 may also be used.

[0055] In some embodiments, R 11 It may be -H. In some embodiments, R 11 R may be -CH3. In some embodiments, 11 -CH2CH3 may also be used.

[0056] In a particular embodiment, R 10 and R 11 Together, they may contain at least one carbon atom. In certain embodiments, R10 and R 11 These together may contain at least two carbon atoms.

[0057] In some embodiments, R 14 It may be -H. In some embodiments, R 14 R may be -CH3. In some embodiments, 14 -CH2CH3 may also be used.

[0058] In some embodiments, R 15 It may be -H. In some embodiments, R 15 R may be -CH3. In some embodiments, 15 -CH2CH3 may also be used.

[0059] In a particular embodiment, R 14 and R 15 Together, they may contain at least one carbon atom. In certain embodiments, R 14 and R 15 These together may contain at least two carbon atoms.

[0060] In some embodiments, m, n, and p may each be 0, R 6 , R 7 , R 22 , R 23 , R 29 , and R 30 These may each be absent. In other embodiments, m, n, and p may each be 1.

[0061] In certain embodiments, m is 1. In some embodiments, R 6 It may be -H. In some embodiments, R 6 R may be -CH3. In some embodiments, 6 R may be -CH2CH3. In some embodiments, 6 -CN 、-C(O)N(CH3)2, -CH2C(O)N(CH3)2, -CO2CH3, or -CH2CO2CH3 may also be used. In some embodiments, R 6 R may be -CO2CH3 or -CH2CO2CH3. In some embodiments, R 6 R may be -CO2CH3. In some embodiments, 7 It may be -H. In some embodiments, R 7 R may be -CH3. In some embodiments, 7 R may be -CH2CH3. In some embodiments, 7 -CN 、 -C(O)N(CH3)2, -CH2C(O)N(CH3)2, -CO2CH3, or -CH2CO2CH3 may also be used. In some embodiments, R 7 R may be -CO2CH3 or -CH2CO2CH3. In some embodiments, R 7 It may also be -CO2CH3.

[0062] In certain embodiments, n is 1. In some embodiments, R 22 It may be -H. In some embodiments, R 22 R may be -CH3. In some embodiments, 22 R may be -CH2CH3. In some embodiments, 23 It may be -H. In some embodiments, R 23 R may be -CH3. In some embodiments, 23 -CH2CH3 may also be used.

[0063] In certain embodiments, p is 1. In some embodiments, R 29 It may be -H. In some embodiments, R 29 R may be -CH3. In some embodiments, 29 R may be -CH2CH3. In some embodiments, 30It may be -H. In some embodiments, R 30 R may be -CH3. In some embodiments, 30 -CH2CH3 may also be used.

[0064] In any embodiment, R 4 , R 5 , R 12 , R 13 , R 20 , R 21 , R 31 , R 32 , R 33 , and R 34 These are, independently, -H, -CN, -CH3, -CH2CH3, -OCH3, -OCH2CH3, -C(O)CH3, -C(O)CH2CH 3、 -CH2C(O)CH3, -CH2COCH2CH 3、 -C(O)2H, -CO2CH3, -CO2CH2CH3, -CH2CO2CH3, -CH2CO2CH2CH3, -NH2, -CH(CH3)NH2, -CH2CH (CH3)NH2, -CH(CH3)CH2NH2, -C(CH3)2NH2, -CH2C(CH3)2NH2, -C(CH3)2CH2NH2, -CH2NH2, -C H2CH2NH2, -CH2CH2CH2NH2, -N(CH3)2, -N(CH2CH3)2, -CH2N(CH3)2, -CH2N(CH2CH3)2, -C(O )N(CH3)2, -C(O)N(CH2CH3)2, -CH2C(O)NH2, -CH2C(O)N(CH3)2, -CH2C(O)N(CH2CH3)2, C4-C 12 (hetero)aryl, C2-C8 (hetero)cycloalkyl, It could also be TIFF2026062912000009.tif57161.

[0065] In some embodiments, R 4 , R 5 , R 12 , R 13 , R 20 , R 21 , R 31 , R 32 , R 33 , and R34 These may each be -H. In some embodiments, R 4 , R 5 , R 12 , R 13 , R 20 , R 21 , R 31 , R 32 , R 33 , and R 34 These may be -H or -CN, independently of each other. In some embodiments, R 4 , R 5 , R 12 , R 13 , R 20 , R 21 , R 31 , R 32 , R 33 , and R 34 These may be independently -H, -CH3, or -CH2CH3. In some embodiments, R 4 , R 5 , R 12 , R 13 , R 20 , R 21 , R 31 , R 32 , R 33 , and R 34 These may each be independently -H, -OCH3, or -OCH2CH3. In some embodiments, R 4 , R 5 , R 12 , R 13 , R 20 , R 21 , R 31 , R 32 , R 33 , and R 34 These are independently -H, -C(O)CH3, and -C(O)CH2CH 3、 -CH2C(O)CH3 or -CH2C(O)CH2CH3 may also be used. In some embodiments, R 4 , R 5 , R 12 , R 13 , R 20 , R 21 , R 31 , R 32, R 33 , and R 34 Each of these may independently be -H, -C(O)2H, -CO2CH3, -CO2CH2CH3, -CH2CO2CH3, or -CH2CO2CH2CH3. In some embodiments, R 4 , R 5 , R 12 , R 13 , R 20 , R 21 , R 31 , R 32 , R 33 , and R 34 Each of these may independently be -H, -NH2, -CH(CH3)NH2, -CH2CH(CH3)NH2, -CH(CH3)CH2NH2, -C(CH3)2NH2, -CH2C(CH3)2NH2, -C(CH3)2CH2NH2, -CH2NH2, -CH2CH2NH2, -CH2CH2CH2NH2, -N(CH3)2, -N(CH2CH3)2, -CH2N(CH3)2, or -CH2N(CH2CH3)2. In some embodiments, R 4 , R 5 , R 12 , R 13 , R 20 , R 21 , R 31 , R 32 , R 33 , and R 34 Each of these may independently be -H, -C(O)N(CH3)2, -C(O)N(CH2CH3)2, -CH2C(O)NH2, -CH2C(O)N(CH3)2, or -CH2C(O)N(CH2CH3)2. In some embodiments, R 4 , R 5 , R 12 , R 13 , R 20 , R 21 , R 31 , R 32 , R 33 , and R 34 These are, independently, -H and C4-C. 12 (Hetero)aryl or C2-C8 (hetero)cycloalkyl. In some embodiments, R 4 , R5 , R 12 , R 13 , R 20 , R 21 , R 31 , R 32 , R 33 , and R 34 These are, independently, -H, It may also be TIFF2026062912000010.tif20128. In some embodiments, R 4 , R 5 , R 12 , R 13 , R 20 , R 21 , R 31 , R 32 , R 33 , and R 34 These are, independently, -H, It may also be TIFF2026062912000011.tif43146.

[0066] In certain embodiments, the compound is the compound of formula I. In some embodiments, R 4 , R 5 , R 33 , and R 34 These are, independently, -H, -CN, -CH3, -CH2CH3, -C(O)CH3, and -C(O)CH2CH 3、 -CH2C(O)CH3, -CH2COCH2CH 3、 -CO2H, -CO2CH3, -CO2CH2CH3, -CH2CO2CH3, -CH2CO2CH2CH3, -C(O)N(CH3)2, -C(O)N(CH2CH3)2, -CH2C(O)NH2, -CH2C(O)N(CH3)2, -CH2C(O)N(CH2CH3)2, It may also be TIFF2026062912000012.tif35165. In some embodiments, R 4 , R 5 , R 33 , and R 34Each of these may independently be -H, -CN, -CH3, -CH2CH3, -C(O)CH3, -CH2C(O)CH3, -CO2H, -CO2CH3, -CH2CO2CH3, or -C(O)N(CH3)2. In certain embodiments, R 4 , R 5 , R 33 , and R 34 At least one of them does not have to be H. In other embodiments, R 4 , R 5 , R 33 , and R 34 These can each be -H.

[0067] In some embodiments, R 4 -H is also acceptable.

[0068] In some embodiments, R 5 This can be -H, -CO2H, or -CO2CH3.

[0069] In some embodiments, R 4 is also -H, R 5 , R 33 , and R 34 At least one of them does not have to be -H.

[0070] In some embodiments, R 4 and R 5 -H is also acceptable.

[0071] In some embodiments, X is CR 33 R 34 It may also be R 33 R may be -H or -CO2CH3. In some embodiments, 34 X may be -H, -CN, -CH3, -C(O)CH3, -CO2CH3, -CH2CO2CH3, or -C(O)N(CH3)2. In some embodiments, X may be O.

[0072] In some embodiments, R6 and R 7 These are -H, -CH3, -CH2CH3, and -CN, respectively, independently. 、 -C(O)N(CH3)2, -CH2C(O)N(CH3)2, -C(O)N(CH2CH3)2, -CH2C(O)N(CH2CH3)2, -CO2CH3, or -CH2CO2CH3. In some embodiments, R 6 R may be -H, 7 -CN 、 -C(O)N(CH3)2, -CH2C(O)N(CH3)2, -C(O)N(CH2CH3)2, -CH2C(O)N(CH2CH3)2, -CO2CH3, or -CH2CO2CH3. In some embodiments, R 6 R may be -H, 7 It may also be -CO2CH3.

[0073] In a particular embodiment, R 4 , R 5 , R 33 , and R 34 -H may also be R 6 and R 7 At least one of them does not have to be -H.

[0074] In some embodiments, R 1 R may be -CH3 or -CH2CH3, 2 R may be H or -CH3, 3 R may be -CH3 or -CH2CH3, 4 R may be -H, 5 may be -H or -CO2CH3, and m may be 0. In some embodiments, R 1 R may be -CH3 or -CH2CH3, 2 R may be H or -CH3, 3 R may be -CH3 or -CH2CH3, 4 R may be -H, 5may be -H, X may be O, and m may be 0. In some embodiments, R 1 R may be -CH3 or -CH2CH3, 2 R may be H or -CH3, 3 R may be -CH3 or -CH2CH3, 4 R may be -H, 5 X may be -H, -CO2CH3, or -CN, and X is CR 33 R 34 It may be R 33 It may be H, and R 34 m may be -H, -CH3, -CO2CH3, or -CN, and m may be 0.

[0075] In some embodiments, R 2 and R 3 Together, they preferably contain at least two carbon atoms.

[0076] In some embodiments, R 4 , R 5 , R 33 , and R 34 At least one of these may be -CH3, -CO2CH3, or -CN. In some embodiments, R 4 , R 5 , R 33 , and R 34 One of these may be -CH3, -CO2CH3, or -CN, and the rest may be -H.

[0077] In some embodiments, the compound of formula I may be one of the following compounds: TIFF2026062912000013.tif130150.

[0078] In some embodiments, the compound of formula I may be one of the following compounds: TIFF2026062912000014.tif40128.

[0079] In some embodiments, the compound of formula I may be one of the following compounds: TIFF2026062912000015.tif87166.

[0080] In some embodiments, R 4 and R 5 They are together and not a divalent group (for example, C=CH2).

[0081] In certain embodiments, the compound is the compound of formula II.

[0082] In some embodiments, R 12 -H is also acceptable.

[0083] In some embodiments, R 13 -H, -CH3, -CH2CH3, -CN 、 -C(O)N(CH3)2, -CH2C(O)N(CH3)2, -C(O)N(CH2CH3)2, -CH2C(O)N(CH2CH3)2, -CO2CH3, or -CH2CO2CH3. In some embodiments, R 13 This can be -H or -CH3.

[0084] In some embodiments, R 14 In other embodiments, R 14 It may also be -CH3.

[0085] In some embodiments, R 16 -OCH3, -OCH2CH3, -N(CH3)2, -N(CH2CH3)2, It may also be TIFF2026062912000016.tif43134. In some embodiments, R 16 is -OCH3, -N(CH3)2, or It may also be TIFF2026062912000017.tif19128.

[0086] In some embodiments, R8 R may be -CH3 or -CH2CH3. In some embodiments, 9 R may be -CH3 or -CH2CH3. In some embodiments, 8 and R 9 R may be -CH3. In some embodiments, 8 and R 9 R may be -CH2CH3. In some embodiments, 10 R may be -H or -CH3. In some embodiments, 11 R may be -CH3 or -CH2CH3. In some embodiments, 10 R may be -H, 11 R may be -CH2CH3. In some embodiments, 10 and R 11 R may be -CH3. In some embodiments, 12 , R 13 , R 14 , and R 15 These may be independently -H or -CH3. In some embodiments, R 12 , R 13 , R 14 , and R 15 -H may also be used. In some embodiments, R 12 , R 13 , R 14 , and R 15 At least one of them may be -CH3. In some embodiments, R 12 , R 13 , R 14 , and R 15 These may each be -CH3. In some embodiments, R 12 and R 13 R may be -H, 14 and R 15 These may each be -CH3. In some embodiments, R 12 and R 13 R may be -CH3, 14 and R 15-H is also acceptable.

[0087] In some embodiments, the compound of formula II may be one of the following compounds: TIFF2026062912000018.tif19133TIFF2026062912000019.tif201134TIFF2026062912000020.tif184152TIFF2026062912000021.tif54149.

[0088] In some embodiments, the compound of formula II may be one of the following compounds: TIFF2026062912000022.tif138159.

[0089] In some embodiments, the compound of formula II may be one of the following compounds: TIFF2026062912000023.tif67159.

[0090] In some embodiments, the compound of formula II may be one of the following compounds: TIFF2026062912000024.tif19138.

[0091] In some embodiments, the compound of formula II may be one of the following compounds: TIFF2026062912000025.tif18128.

[0092] In certain embodiments, the compound is the compound of formula III. In some embodiments, R 18 and R 19 Each of these may independently be -H or -C1-C6 alkyl. In some embodiments, R 18 and R 19 Each of these may independently be -H or -C1-C4 alkyl. In some embodiments, R 18 and R 19Each of these may independently be -H or -C1-C3 alkyl. In some embodiments, R 18 It may be -H. In some embodiments, R 19 This can be -H or -CH3.

[0093] In some embodiments, R 20 and R 21 These are, independently, -H, -CN, -CH3, -CH2CH3, -C(O)CH3, and -C(O)CH2CH 3、 -CH2C(O)CH3, -CH2COCH2CH 3、 -C(O)2H, -CO2CH3, -CO2CH2CH3, -CH2CO2CH3, -CH2CO2CH2CH3, -C(O)N(CH3)2, -C(O)N(CH2CH3)2, -CH2C(O)NH2, -CH2C(O)N(CH3)2, -CH2C(O)N(CH2CH3)2, -C4-C 12 (hetero)aryl, -C2-C8 (hetero)cycloalkyl, TIFF2026062912000026.tif43128 is also acceptable.

[0094] In some embodiments, R 24 and R 25These are, independently, -H, -CN, -C1-C4 alkyl, -C2-C6 (hetero)cycloalkyl, -CH2-O-C1-C4 alkyl, -C(O)-C1-C4 alkyl, -C1-C4 alkyl -C(O)-C1-C4 alkyl, -C(O)-C2-C6 (hetero)cycloalkyl, -C1-C4 alkyl -C(O)-C2-C6 (hetero)cycloalkyl, -CO2H, -CO2-C1-C4 alkyl, -C1-C4 alkyl -CO2-C1-C4 alkyl, -CO2-C2-C6 (hetero)cycloalkyl Kill, -C1-C4 alkylene-CO2-C2-C6(hetero)cycloalkyl, -C1-C4 alkylene-NH2, -C1-C4 alkylene-NH-C1-C4 alkyl, -C1-C4 alkylene-N(C1-C4 alkyl)2, -C(O)NH2, -C1-C4 alkylene-C(O)NH2, -C(O)NH-C1-C4 alkyl, -C(O)N(C1-C4 alkyl)2, -C1-C4 alkylene-C(O)NH-C1-C4 alkyl, -C1-C4 alkylene-C(O)N(C1-C4 alkyl)2, -C4-C 12 It may also be a (hetero)aryl or -C3-C6 (hetero)cycloalkyl group.

[0095] In some embodiments, R 20 , R 21 , R 24 , and R 25 Each of these may independently be -H, -CN, -CH3, -CH2CH3, -C(O)CH3, -CH2C(O)CH3, -CO2CH3, -CH2CO2CH3, -C(O)N(CH3)2, phenyl, cyclopentyl, or cyclohexyl.

[0096] In some embodiments, R 20 R may be -H, -CH3, -CH2CH3, -CO2CH3, or phenyl. In some embodiments, R 20 It may be -H. In some embodiments, R 21 R may be -H, -CH3, -CH2CH3, -CO2CH3, or phenyl. In some embodiments, R 21n may be -CH3, -CH2CH3, -CO2CH3, or phenyl. In some embodiments, n may be 0, and R 22 and R 23 It may be absent. In other embodiments, n may be 1, and R 22 and R 23 -H is also acceptable.

[0097] In some embodiments, R 24 R may be -H, -CN, -C(O)CH3, -CO2CH3, -CH2CO2CH3, -C(O)N(CH3)2, phenyl, cyclopentyl, or cyclohexyl. In some embodiments, R 24 R may be -H, -CN, -C(O)CH3, -CO2CH3, -CH2CO2CH3, -C(O)N(CH3)2, phenyl, cyclopentyl, or cyclohexyl. In some embodiments, R 25 This may be -CN, -C(O)CH3, -CO2CH3, -CH2CO2CH3, -C(O)N(CH3)2, phenyl, cyclopentyl, or cyclohexyl.

[0098] In some embodiments, R 18 R may be -H, 19 R may be -H or -CH3, 20 R may be -H, 21 R may be -H or -CO2CH3, 22 and R 23 It is acceptable for them to be absent, R 24 R may be -H or -CO2CH3, 25 R may be -CN, -C(O)CH3, -CO2CH3, -CH2CO2CH3, or -C(O)N(CH3)2. In some embodiments, R 24 R may be -H, 25 R may be -CN, -C(O)CH3, -CO2CH3, or -C(O)N(CH3)2. In some embodiments, R 24 R may be -CO2CH3, 25This can be -CN, -CO2CH3, or -CH2CO2CH3.

[0099] In some embodiments, R 24 R may be -H, -CH3, -CH2CH3, -CO2CH3, or phenyl. In some embodiments, R 24 It may be -H. In some embodiments, R 25 R may be -H, -CH3, -CH2CH3, -CO2CH3, or phenyl. In some embodiments, R 25 n may be -CH3, -CH2CH3, -CO2CH3, or phenyl. In some embodiments, n may be 0, and R 22 and R 23 It may be absent. In other embodiments, n may be 1, and R 22 and R 23 It can be -H.

[0100] In some embodiments, R 20 R may be -H, -CN, -C(O)CH3, -CO2CH3, -CH2CO2CH3, -C(O)N(CH3)2, phenyl, cyclopentyl, or cyclohexyl. In some embodiments, R 20 R may be -H, -CN, -C(O)CH3, -CO2CH3, -CH2CO2CH3, -C(O)N(CH3)2, phenyl, cyclopentyl, or cyclohexyl. In some embodiments, R 21 This may be -CN, -C(O)CH3, -CO2CH3, -CH2CO2CH3, -C(O)N(CH3)2, phenyl, cyclopentyl, or cyclohexyl.

[0101] In some embodiments, R 18 R may be -H, 19 R may be -H or -CH3, 24 R may be -H, 25 R may be -H or -CO2CH3, 22 and R 23It is acceptable for them to be absent, R 20 R may be -H or -CO2CH3, 21 R may be -CN, -C(O)CH3, -CO2CH3, -CH2CO2CH3, or -C(O)N(CH3)2. In some embodiments, R 20 is also -H, R 21 R may be -CN, -C(O)CH3, -CO2CH3, or -C(O)N(CH3)2. In some embodiments, R 20 R may be -CO2CH3, 21 This can be -CN, -CO2CH3, or -CH2CO2CH3.

[0102] In some embodiments, the compound of formula III may be one of the following compounds: TIFF2026062912000027.tif100162TIFF2026062912000028.tif184156.

[0103] In some embodiments, the compound of formula III may be one of the following compounds: TIFF2026062912000029.tif105163.

[0104] In certain embodiments, the compound is the compound of formula IV. In some embodiments, R 27 and R 28 These are, independently, -H or -Z-NR 35 R 36 It may also be R 27 R may be -H, 28 is, -Z-NR 35 R 36 It may also be R 28 is, -Z-NR 35 R 36 It may also be. In some embodiments, Z may be a C1-C alkylene. In some embodiments, Z may be a C1-C4 alkylene. In some embodiments, R28 R may be -CH(CH3)NH2, -CH(CH3)CH2NH2, -C(CH3)2NH2, -C(CH3)2CH2NH2, -CH2NH2, -N(CH3)2, or -N(CH2CH3)2. In some embodiments, R 28 This can also be -C(CH3)2NH2.

[0105] In some embodiments, R 35 and R 36 Each of these may independently be -H, -C1-C6 alkyl, -C1-C6 alkylene-OH, -C1-C6 alkylene-NH2, -C1-C6 alkylene-NH-C1-C6 alkyl, or -C1-C6 alkylene-N-(C1-C6 alkyl)2. In some embodiments, R 35 and R 36 Each of these may independently be -H, -C1-C2 alkyl, -C1-C2 alkylene-OH, -C1-C2 alkylene-NH2, -C1-C2 alkylene-NH-C1-C2 alkyl, or -C1-C2 alkylene-N-(C1-C2 alkyl)2. In some embodiments, R 35 and R 36 Each of these may independently be -H or -C1-C2 alkyl. In some embodiments, R 35 and R 36 R may be the same. In some embodiments, 35 and R 36 They may be different.

[0106] In some embodiments, p may be 0, R 29 and R 30 They may be absent.

[0107] In some embodiments, R 31 and R 32Each of these may independently be -H, -C(O)2H, -CO2CH3, -C(O)N(CH3)2, -C(O)N(CH2CH3)2, -CH2C(O)NH2, -CH2C(O)N(CH3)2, or -CH2C(O)N(CH2CH3)2. In some embodiments, R 31 and R 32 -H is also acceptable.

[0108] In any embodiment, the compound may be a low-volatile organic compound (low-VOC).

[0109] In any embodiment, the compound of formula I, II, III, or IV has a boiling point greater than about 225°C. In any embodiment, the compound has a boiling point of at least about 250°C. In any embodiment, the compound has a boiling point of at least about 260°C. In any embodiment, the compound has a boiling point of at least about 270°C. In any embodiment, the compound has a boiling point of at least about 280°C.

[0110] In any embodiment, the compounds of formulas I, II, III, or IV have a longer gas chromatography retention time than diethyl adipate. In any embodiment, the gas chromatography (GC) retention time may be measured according to the GB18582 test method. In any embodiment, the gas chromatography retention time may be measured using a polydimethylsiloxane capillary column (30 m × 0.32 mm × 1.0 μm) with an initial temperature of 45°C, an inlet temperature of 260°C, a detector temperature of 280°C, and a detector temperature of 230°C. In any embodiment, the initial temperature may be held for 4 minutes, followed by an increase of 8°C per minute. In any embodiment, the GC retention time of the compound may be at least about 0.5 seconds longer than that of diethyl adipate. In any embodiment, the GC retention time of the compound may be at least about 1.0 second longer than that of diethyl adipate. In any embodiment, the compound has a longer GC retention time than hexadecane. In any embodiment, the GC retention time of the compound may be at least about 0.5 seconds longer than that of hexadecane. In any embodiment, the GC retention time of the compound may be at least about 1.0 second longer than that of hexadecane. In any embodiment, the compound has a longer GC retention time than that of methyl palmitate. In any embodiment, the GC retention time of the compound may be at least about 0.5 seconds longer than that of methyl palmitate. In any embodiment, the GC retention time of the compound may be at least about 1.0 second longer than that of methyl palmitate.

[0111] In any embodiment, the compound has lower toxicity than N-methyl-2-pyrrolidione. While we do not wish to be bound by theory, it is hypothesized that the toxicity of NMP is at least partially caused by oxidation at the C5 position of the pyrrolidinone ring that occurs in the body (Scheme 1). It is hypothesized that this technique, which prevents oxidation at C5, will prevent toxicity or at least result in lower toxicity compared to NMP. TIFF2026062912000030.tif46139

[0112] In another embodiment, the Art provides compositions comprising, in any embodiment disclosed herein, compounds of formulas I, II, III, and IV, or combinations of two or more thereof. In any embodiment, the composition may not substantially contain NMP. In any embodiment, the composition is a composition known to contain NMP, and the compound is replaced by NMP in the composition. In any embodiment, the compound is replaced by NMP in a one-to-one ratio (for example, all moles of NMP are replaced by the names of the moles of the compound).

[0113] In any embodiment, the composition may be substantially free of methylene chloride. In any embodiment, the compound replaces methylene chloride in the composition. In any embodiment, the compound replaces NMP and methylene chloride in the composition.

[0114] In any embodiment, the composition may be a paint or coating, a stripper (e.g., paints, photoresists, furniture, graffiti, wheels, nail polish remover), a cleaner (e.g., ovens, surfaces, floors, automobiles, industrial, optical, printed circuit boards, or semiconductors), an adhesive / binder / sealant, for leather treatment, for personal care (i.e., commonly used as a surfactant), for screen printing (e.g., lithography, silk), for pharmaceutical formulations, and / or for manufacturing (e.g., electronic devices such as printed circuit boards, flux removers, or semiconductors, pharmaceuticals, agrochemicals, petrochemicals, plasticizers, inks). In any embodiment, the composition may be any composition known to contain NMP. Non-limiting examples include “Preliminary Information on Manufacturing, Processing, Distribution, Use, and Disposal: N-Methylpyrrolidone (NMP),” published by the U.S. EPA (February 2017), which is incorporated herein by reference.

[0115] In some embodiments, the composition may be a paint or coating. In some embodiments, the composition may further include a binder, a pigment and / or a dye, a carrier (e.g., water), a dispersant, or a combination of two or more of these.

[0116] A wide range of pigments and dyes known to those skilled in the art can be used, including black, blue, red, green, yellow, and mixtures thereof. A brief enumeration of some exemplary pigments and dyes may include carbon black, phthalocyanine blue, perylene black, azo dyes including metallized azo dyes, carbocyclic azo dyes and heterocyclic azo dyes, polymethine dyes, quinophthalone, sulfur dyes, nitro and nitroso dyes, cyanines, diazacarbocyanines, anthraquinones, and other pigments.

[0117] In any embodiment, the composition may be a stripper (e.g., paint, photoresist, furniture, graffiti, wheel, nail polish remover). In some embodiments, the compounds in the composition may also be active solvents. In some embodiments, the composition may further include alcohol, water, amines (e.g., monoethanolamine), acids (e.g., hypophosphorous acid and / or glycolic acid), bases (e.g., sodium hydroxide and / or calcium hydroxide), salts (e.g., trisodium phosphate), peroxides, dichloroethylene, ethers (e.g., aromatic ethers), surfactants, corrosion inhibitors, waxes, thickeners, or two or more combinations thereof. In some embodiments, the alcohol may be a C1-C6 alcohol, including phenol and / or C1-C4 alcohols such as propanol, isopropanol, and butanol.

[0118] In any embodiment, the composition may be a cleaner (e.g., for ovens, surfaces, floors, automobiles, industrial, optical, printed circuit boards, or semiconductors). In some embodiments, the composition may further comprise water, a base (e.g., sodium hydroxide, lithium, and / or calcium hydroxide), a surfactant (e.g., a nonionic surfactant, e.g., tridecyloxypolyethyleneoxyethanol and alkylphenoxypolyethoxyethanol), a thickener (e.g., colloidal magnesium aluminum silicates, alginates, ethylene oxide polymers, carboxymethylcellulose, carboxyethylcellulose, bentonite, and / or starch, available under the trademark Veegum T from Vanderbilt Co.), a wetting agent (e.g., glycerol, propylene glycol, and polyethylene glycol, and / or ethanolamines, e.g., triethanolamine, diethanolamine, and / or monoethanolamine), an organic solvent (e.g., ethylene glycol monophenyl ether, methoxypolyethylene glycol, tripropylene glycol methyl ether, diethylene glycol monophenyl ether, diethylene glycol monobutyl ether, phenyl glycol ether, and / or ethanol), alkali metal carbonates and / or bicarbonates, metal chelating agents, ammonium fluoride, or two or more combinations thereof.

[0119] In any embodiment, the composition may be an adhesive / binder / sealant. In some embodiments, the composition may further include resins / polymers, organic solvents (e.g., THF, MEK, C1-C6 alcohols, acetone, methyl acetate, etc.), water, pigments and / or dyes, fillers, thixotropes, plasticizers, lime, cement, gypsum, liquid glass, carbohydrates (e.g., cellulose and its derivatives, starch, etc.), waxes, linseed oil, gum arabic, gum, casein, or two or more combinations thereof.

[0120] In any embodiment, the composition may be for leather treatment. In some embodiments, the composition may further include organic solvents (e.g., naphtha and / or turpentine oil), oils (e.g., beef tallow and / or mink oil), waxes, pigments and / or dyes, or two or more combinations thereof.

[0121] In any embodiment, the composition may be for personal care (i.e., commonly used as a surfactant). In some embodiments, the composition may further include water, alpha hydroxy acids, polyhydroxy acids, hydroquinones, retinols, kojic acid, copper peptides, vitamins, minerals, humectants, emollients, wetting agents, lubricants, sensates, fragrances, anti-dandruff agents, buffers, bulking agents, chelating agents, colorants, astringents, cosmetic biocides, denaturants, anti-inflammatory agents, sunscreens, film-forming agents, polymers, pH adjusters, propellants, reducing agents, sequestrants, conditioning agents, thickeners, cleansing agents, or two or more combinations thereof.

[0122] In any embodiment, the composition may be a screen printing composition (e.g., lithography, silk). In some embodiments, the composition may further include a binder, a pigment and / or dye, a carrier (e.g., an organic solvent such as water, C1-C6 alcohols, dichloropropane, toluene, acetone, xylene and their derivatives), a dispersant, or two or more combinations thereof.

[0123] In any embodiment, the composition may be a pharmaceutical formulation. In some embodiments, the composition may further comprise a pharmaceutically acceptable carrier (e.g., water), an active drug, a preservative, or a combination of two or more thereof.

[0124] In any embodiment, the compositions described herein can be used for manufacturing purposes (e.g., electronic devices such as printed circuit boards, flux removers, or semiconductors, pharmaceuticals, agrochemicals, petrochemicals, plasticizers, inks, etc.).

[0125] In any embodiment, the composition may be any composition that requires acid neutralization. In any embodiment, the composition may be any composition that requires pH elevation. In some embodiments, the composition may have a pH of about 8 to 10.

[0126] In any embodiment, the composition does not have to be an electrolyte composition. In any embodiment, the compound does not have to be an electrolyte in the composition. In any embodiment, the composition does not have to be a microwave dielectric heating medium. In any embodiment, the composition does not have to be a contact lens or its precursor.

[0127] In another embodiment, the present invention provides a method for producing compounds of formulas I, II, III, and IV. 1 ~R 36 X, Z, m, n, and p are as defined herein.

[0128] In any embodiment, a method for producing a compound of formula I involves reacting a nitroalkane with an acrylate reagent to form a nitroalkanoyl reagent, optionally derivatizing the nitroalkanoyl reagent, reducing the nitroalkanoyl reagent to form an aminoalkanoyl reagent, optionally derivatizing the aminoalkanoyl reagent, and cyclizing the aminoalkanoyl reagent to produce a compound of formula Ia. This may include forming TIFF2026062912000031.tif52128 and alkylating the compound of formula Ia to form the compound of formula I.

[0129] In any embodiment, the nitroalkane may be a compound of formula Ib: TIFF2026062912000032.tif27128.

[0130] In any embodiment, the acrylate reagent may be a compound of formula IC, In formula TIFF2026062912000033.tif41128, LG may be any known leaving group, including those described herein.

[0131] In another embodiment, a method for producing a compound of formula I involves reacting a nitroalkane with a ketone or aldehyde to form a nitro alcohol, optionally derivatizing the nitro alcohol, reducing the nitro alcohol to form an amino alcohol, optionally derivatizing the amino alcohol, and cyclizing the amino alcohol in the presence of carbon dioxide to produce a compound of formula Id. This may include forming TIFF2026062912000034.tif48128 and alkylating the compound of formula Id to form the compound of formula I.

[0132] In any embodiment, the nitroalkane may be a compound of formula Ib: TIFF2026062912000035.tif27128.

[0133] In any embodiment, the ketone or aldehyde may be a compound of formula Ie: TIFF2026062912000036.tif29128.

[0134] In any embodiment, a method for producing a compound of formula II includes reacting a nitroalkane with an acrylate reagent to form a nitroalkanoyl reagent, optionally derivatizing the nitroalkanoyl reagent, and reducing the nitroalkanoyl reagent to form a compound of formula IIa. This may include forming TIFF2026062912000037.tif35128 and alkylating the compound of formula IIa to form the compound of formula II.

[0135] In any embodiment, the nitroalkane may be a compound of formula IIb: TIFF2026062912000038.tif27128.

[0136] In any embodiment, the acrylate reagent may be a compound of formula IIc: TIFF2026062912000039.tif41128.

[0137] In any embodiment, a method for producing the compound of formula III may include reducing a nitroalkane to form an alkylhydroxylamine, reacting the alkylhydroxylamine with an aldehyde to form a nitrone, and reacting the nitrone with an alkene to form the compound of formula III.

[0138] In any embodiment, the nitroalkane may be a compound of formula IIIb: TIFF2026062912000040.tif13128.

[0139] In any embodiment, nitrone may be a compound of formula IIIc: TIFF2026062912000041.tif40128.

[0140] In any embodiment, the alkene may be a compound of formula IIId: TIFF2026062912000042.tif32128.

[0141] In any embodiment, a method for producing the compound of formula IV may include reacting a nitroalkane with maleimide to form a nitropyrrolidine-dione, and reducing the nitropyrrolidine-dione to form the compound of formula IV.

[0142] In any embodiment, nitropyrrolidine-dione may be a compound of formula IVb: TIFF2026062912000043.tif66128.

[0143] In any embodiment, one or more steps described in any method herein may be carried out in a single pot. In any embodiment, two or more steps described in any method herein may be carried out in a single pot. In any embodiment, three or more steps described in any method herein may be carried out in a single pot.

[0144] In some embodiments, intermediate products prepared by any method herein may be used in subsequent steps without purification. In other embodiments, intermediate products prepared by any method herein may be purified before use in subsequent steps. In any embodiment, one or more intermediate products and / or final products may be purified by known techniques including filtration, centrifugation, chromatography, evaporation, liquid-liquid extraction, distillation (e.g., vacuum distillation), sublimation, crystallization, or two or more combinations thereof. In any embodiment, purification may include distillation.

[0145] The examples described herein are provided to illustrate the advantages of the Art and to further assist those skilled in the art in preparing or using the compounds of the Art or their salts, racemic mixtures, or tautomers. Examples are also presented herein to more fully illustrate preferred embodiments of the Art. The examples should not be construed as limiting the scope of the Art as defined by the appended claims. The examples may include or incorporate any of the above-described variations, embodiments, or embodiments(s) of the Art. Each of these variations, embodiments, or embodiments(s) may further include or incorporate variations of any or all other variations, embodiments, or embodiments(s) of the Art. [Examples]

[0146] Example 1: Synthesis of the compound of formula I when X is carbon. As shown in Scheme 2, methacrylate (acrylate reagent) and 2-nitropropane (nitroalkane) were reacted in the presence of a base, followed by hydrogenation to produce methyl-4-amino-4-methylpentanoate (aminoalkanoyl reagent). Next, methyl-4-amino-4-methylpentanoate was cyclized to form 5,5-dimethylpyrrolidine-2-one (compound of formula Ia), followed by methylation to produce 1,5,5-trimethylpyrrolidine-2-one.

[0147] Specifically, a reflux condenser and an addition funnel were attached to a 2-liter multi-necked round-bottom flask. 5.0 g (0.043 mol) of 1,1,3,3-tetramethylguanidine (TMG, 99%, Aldrich) was packed into the flask. The addition funnel was filled with a mixture of 405 g (4.55 mol) of 2-nitropropane (2NP, 98+%, ANGUS Chemical Co.) and 383 g (4.45 mol) of methyl acrylate (MA, 99%, containing less than 100 ppm of monomethyl etherhydroquinone (Aldrich) as an inhibitor). The 2NP / MA mixture was gradually added to the flask while stirring. The contents of the reactor were heated to 110°C by an exothermic reaction. The 2NP / DMAA mixture was added to the flask at a rate maintaining a temperature of 105-110°C. After the 2NP / MA mixture was completely added, the mixture was stirred at 110°C for 30 minutes. GC analysis showed that over 99% of the MA was converted to a cyan-colored liquid nitroester.

[0148] 100 g of water, 200 g of methanol, and 30 g of wet Raney® nickel were added to a 2 L Parr reactor. The reactor was purged with hydrogen. The nitroester obtained from the previous reaction was added to the reactor while stirring and maintaining the temperature at 65°C. After the addition of the nitroester was complete, the reagents were stirred and reacted at 65°C for 30 minutes, followed by cooling to 25°C. The reactor was evacuated and the catalyst was filtered off from the product. The catalyst was rinsed with 250 g of water, and the filtrate was concentrated by heating to 150°C under atmospheric pressure. Once the temperature reached 150°C, a vacuum of 150 mmHg was applied. The temperature and vacuum were maintained for 1 hour until condensation stopped and the reaction mixture was completely liquefied. The product was isolated and purified using vacuum distillation to obtain the product, which solidified when left at room temperature. The isolated yield was 425 g of colorless solid (84.4% yield from methyl acrylate). 1 The 1H NMR (D2O) was consistent with the assigned structure. The purity was 99.5% by GC-FID.

[0149] In a 1-liter round-bottom flask, 210 g (1.86 mol) of 5,5-dimethyl-2-pyrrolidinone and 210 g (2.59 mol) of formaldehyde (Fisher Scientific, 37% aqueous solution) were added, followed by 2.1 g of sodium hydroxide (50% aqueous solution). The mixture was stirred at ambient temperature for 16 hours. The reaction mixture was dealkalized using ion-exchange chromatography at a flow rate of 10 mL / min: Dowex MAC-3H type, 60 × 2 cm column (bed volume 120 mL, washed with 4-6 BV water). The eluate was neutral to the pH strip. The product was concentrated at 100 °C and 20 mmHg for 1 hour to obtain 255 g of a pale yellow liquid. The isolation yield was 96.0%. The product was purified to over 98% by GC-FID. 1 H NMR (400MHz, D2O): δ = 4.66 (s, 2H), 2.36 (t, 2H), 1.83 (t, 2H), 1.21 (s, 6H).

[0150] 1,5,5-trimethylpyrrolidine-2-one was produced by hydrogenolysis of 1-(hydroxymethyl)-5,5-dimethylpyrrolidine-2-one (according to J. Auerbach, M. Zamore, and S.M. Weinreb, J. Org. Chem. 1976, 41(4), 725-726) in a yield of 48% as determined by GC-FID analysis. TIFF2026062912000044.tif41166

[0151] Example 2: Synthesis of the compound of formula I when X is oxygen. As shown in Scheme 3, formaldehyde and 2-nitropropane were reacted and subsequently hydrogenated to produce 2-amino-2-methylpropan-1-ol (amino alcohol). Next, 2-amino-2-methylpropan-1-ol was reacted with carbon dioxide to produce 4,4-dimethyloxazolidine-2-one (compound of formula Id). Then, 4,4-dimethyloxazolidine-2-one was methylated to produce 3,4,4-trimethyloxazolidine-2-one. TIFF2026062912000045.tif43169

[0152] Example 3: Synthesis of the compound of formula II. As shown in Scheme 4, N,N-dimethylacrylamide (acrylate reagent) and 2-nitropropane (nitroalkane) were reacted in the presence of a base to produce N,N-4-trimethyl-4-nitropentamide (nitroalkanoyl reagent). Next, N,N-4-trimethyl-4-nitropentamide was hydrogenated to form 4-amino-N,N,4-trimethylpentanamide (compound of formula IIa), which was then methylated to produce 4-(dimethylamino)-N,N-4-trimethylpentamide.

[0153] Specifically, a reflux condenser and an addition funnel were attached to a 2-liter multi-necked round-bottom flask. The flask was filled with 8.75 g (0.76 mol) of 1,1,3,3-tetramethylguanidine (TMG, 99%, Aldrich). 425 g (4.77 mol) of 2-nitropropane (2NP, 98+%, ANGUS Chemical Co.) and 450 g (4.54 mol) of N,N-dimethylacrylamide (DMAA, 99%, containing 500 ppm monomethyl etherhydroquinone (Aldrich) as an inhibitor) were added to the addition funnel. The 2NP / DMAA mixture was gradually added to the flask while stirring. The contents of the reactor were heated to 75°C by an exothermic reaction. The 2NP / DMAA mixture was added to the flask at a rate that maintained a temperature of 70-80°C. After the 2NP / DMAA mixture had been completely added, the mixture was stirred at 75°C for 8 hours. GC analysis showed that 98% of the DMAA was converted to a yellow liquid nitroamide.

[0154] The obtained nitroamide was added to a 2 L Parr reactor along with 300 g methanol and 30 g wet Raney® nickel. The reactor was purged with hydrogen. The reagents were stirred and reacted at 65°C and 750 psig of hydrogen. In a separate vessel, a mixture of 400 g (2.13 mol) nitroamide (prepared in the previous example) and 431 g (5.31 mol) formaldehyde (37% aqueous solution, Fisher Scientific) was prepared. The nitroamide / formaldehyde mixture was added to the reactor with stirring while maintaining 65°C. Subsequently, it was flushed with 50 g (0.62 mol) of 37% aqueous formaldehyde solution. The contents of the reactor were held at 65°C for 2 hours, and then cooled to 25°C. The reactor was evacuated, and the catalyst was filtered off from the product. After rinsing the catalyst with methanol (2 × 20 mL), the filtrate was concentrated under vacuum. The product was isolated and purified using vacuum distillation to obtain a pale yellow liquid with a purity of over 99% by GC-FID, recovered from DMAA in 75% yield. The boiling points were measured as 170°C at 40 mmHg, 145°C at 15 mmHg, and 137°C at 10 mmHg. 1¹H NMR (400 MHz, D2O): d = 2.95 (s, 3H), 2.88 (s, 3H), 2.24 (m, 2H), 2.05 (s, 6H), 1.54 (m, 2H), 0.91 (s, 6H). The product was soluble in water and mineral oil, and soluble more in lithium grease, beeswax, asphalt, and dry styrene-acrylic paint than in NMP. TIFF2026062912000046.tif39163

[0155] Example 4: Synthesis of the compound of formula III. As shown in Scheme 5, 2-nitropropane (nitroalkane) was reduced to produce N-isopropylhydroxylamine (alkylhydroxylamine). N-isopropylhydroxylamine was reacted with formaldehyde to form N-isopropylmethaneimine oxide (nitrone), which was then reacted with methyl acrylate (alkene) to produce methyl 2-isopropylisoxazolidine-5-carboxylate. TIFF2026062912000047.tif35170

[0156] Example 5: Synthesis of the compound of formula IV. As shown in Scheme 6, maleimide was reacted with 2-nitropropane (nitroalkane) in the presence of a base to produce 3-(2-nitropropan-2-yl)pyrrolidine-2,5-dione (nitropyrrolidine-dione). Then, 3-(2-nitropropan-2-yl)pyrrolidine-2,5-dione was hydrogenated to produce 3-(2-aminopropan-2-yl)pyrrolidine-2,5-dione. TIFF2026062912000048.tif42166

[0157] Exemplary Embodiments Item 1. Compounds of formula I, formula II, formula III, or formula IV, In formula TIFF2026062912000049.tif110128, X is O or CR 33 R 34 And R 1 , R 8 , R9 , R 17 , and R 26 However, each is independently -CH3, -CH2CH3, -CH2CH2CH3, or -CH(CH3)2, and R 2 , R 3 , R 10 , R 11 , R 14 , and R 15 However, each is independently -H, -CH3, or -CH2CH3, and R 6 and R 7 However, each is independent of the others: absent, -H, -CH3, -CH2CH3, -CN 、 -C(O)N(CH3)2, -CH2C(O)N(CH3)2, -C(O)N(CH2CH3)2, -CH2C(O)N(CH2CH3)2, -CO2CH3, or -CH2CO2CH3, R 16 However, -O-C1-C8 alkyl, -O-C2-C8 (hetero)cycloalkyl, -O-C4-C 12 (hetero)aryl, -NH2, -NH-C1-C8 alkyl, -N(C1-C8 alkyl)2, TIFF2026062912000050.tif45128, R 18 and R 19 However, each is independently -H or -C1-C8 alkyl, and R 22 and R 23 However, each is independently absent, -H, or -C1-C8 alkyl, and R 24 and R 25However, each is independent of -H, -CN, -C1-C8 alkyl, -C2-C8 (hetero)cycloalkyl, -CH2-O-C1-C8 alkyl, -C(O)-C1-C8 alkyl, -C1-C8 alkylene-C(O)-C1-C8 alkyl, -C(O)-C2-C8 (hetero)cycloalkyl, -C1-C8 alkylene-C(O)-C2-C8 (hetero)cycloalkyl, -CO2H, -CO2-C1-C8 alkyl, -C1-C8 alkylene-CO2-C1-C8 alkyl, -CO2-C2-C8 (hetero)cycloalkyl, -C1-C8 Lukilen-CO2-C2-C8(hetero)cycloalkyl, -C1-C8alkylene-NH2, -C1-C8alkylene-NH-C1-C8alkyl, -C1-C8alkylene-N(C1-C8alkyl)2, -C(O)NH2, -C1-C8alkylene-C(O)NH2, -C(O)NH-C1-C8alkyl, -C(O)N(C1-C8alkyl)2, -C1-C8alkylene-C(O)NH-C1-C8alkyl, -C1-C8alkylene-C(O)N(C1-C8alkyl)2, -(hetero)aryl, -(hetero)cycloalkyl, The file is TIFF2026062912000051.tif20128, and R 4 , R 5 , R 12 , R 13 , R 20 , R 21 , R 31 , R 32 , R 33 , and R 34However, each is independent of -H, -CN, -C1-C8alkyl, -C2-C8(hetero)cycloalkyl, -O-C1-C8alkyl, -CH2-O-C1-C8alkyl, -C(O)-C1-C8alkyl, -C1-C8alkyl-C(O)-C1-C8alkyl, -C(O)-C3-C8cycloalkyl, -C1-C8alkyl-C(O)-C2-C8(hetero)cycloalkyl, -CO2H, -CO2-C1-C8alkyl, -C1-C8alkyl-CO2-C1-C8alkyl, -CO2-C2-C8(hetero)cycloalkyl, -C1-C8alkyl-CO2-C2-C 8(hetero)cycloalkyl, -NH2, -C1-C8alkylene-NH2, -NH-C1-C8alkyl, -N(C1-C8alkyl)2, -C1-C8alkylene-NH-C1-C8alkyl, -C1-C8alkylene-N(C1-C8alkyl)2, -C(O)NH2, -C1-C8alkylene-C(O)NH2, -C(O)NH-C1-C8alkyl, -C(O)N(C1-C8alkyl)2, -C1-C8alkylene-C(O)NH-C1-C8alkyl, -C1-C8alkylene-C(O)N(C1-C8alkyl)2, -(hetero)aryl, -(hetero)cycloalkyl, TIFF2026062912000052.tif66134, R 27 and R 28 However, each is independent of -H or -Z-NR 35 R 36 And Z is C1-C8 alkylene, and R 35 and R 36 However, each is independently -H, -C1-C8 alkyl, -(hetero)aryl, -(hetero)cycloalkyl, -C1-C8 alkylene-OH, -C1-C8 alkylene-NH2, -C1-C8 alkylene-NH-C1-C8 alkyl, or -C1-C8 alkylene-N-(C1-C8 alkyl)2, and R 29 and R 30 A compound in which each of the following is independently absent, -H, -CH3, or -CH2CH3, and m, n, and p are each independently 0 or 1.

[0158] Section 2.R 1However, the compound is -CH3 as described in item 1.

[0159] Section 3.R 1 However, the compound is -CH2CH3 as described in item 1.

[0160] Section 4.R 1 The compounds described in item 1, wherein the compound is -CH2CH2CH3 or -CH(CH3)2.

[0161] Section 5.R 8 However, a compound that is -CH3, as described in any one of items 1 to 4.

[0162] Section 6.R 8 However, the compound is -CH2CH3, as described in any one of items 1 to 4.

[0163] Section 7.R 8 A compound described in any one of items 1 to 4, wherein the compound is -CH2CH2CH3 or -CH(CH3)2.

[0164] Section 8.R 9 A compound described in any one of items 1 to 7, wherein the compound is -CH3.

[0165] Section 9.R 9 However, the compound is -CH2CH3, as described in any one of items 1 to 7.

[0166] Section 10.R 9 A compound described in any one of items 1 to 7, wherein the compound is -CH2CH2CH3 or -CH(CH3)2.

[0167] Section 11.R 17 However, a compound that is -CH3, as described in any one of items 1 to 10.

[0168] Section 12.R 17 However, the compound is -CH2CH3, as described in any one of items 1 to 10.

[0169] Section 13.R 17A compound described in any one of items 1 to 10, wherein the compound is -CH2CH2CH3 or -CH(CH3)2.

[0170] Section 14.R 26 However, a compound that is -CH3, as described in any one of items 1 to 13.

[0171] Section 15.R 26 However, the compound is -CH2CH3, as described in any one of items 1 to 13.

[0172] Section 16.R 26 A compound described in any one of items 1 to 13, wherein the compound is -CH2CH2CH3 or -CH(CH3)2.

[0173] Section 17.R 2 A compound described in any one of items 1 to 16, wherein the compound is -H.

[0174] Section 18.R 2 A compound described in any one of items 1 to 16, wherein the compound is -CH3.

[0175] Section 19.R 2 However, the compound is -CH2CH3, as described in any one of items 1 to 16.

[0176] Section 20.R 3 A compound described in any one of items 1 to 19, wherein the compound is -H.

[0177] Section 21.R 3 A compound described in any one of items 1 to 19, wherein the compound is -CH3.

[0178] Section 22.R 3 A compound described in any one of items 1 to 19, wherein the compound is -CH2CH3.

[0179] Section 23.R 10 A compound described in any one of items 1 to 22, wherein the compound is -H.

[0180] Section 24.R 10However, a compound that is -CH3, as described in any one of items 1 to 22.

[0181] Section 25.R 10 However, the compound is -CH2CH3, as described in any one of items 1 to 22.

[0182] Section 26.R 11 A compound described in any one of items 1 to 25, wherein the compound is -H.

[0183] Section 27.R 11 However, a compound that is -CH3, as described in any one of items 1 to 25.

[0184] Section 28.R 11 However, the compound is -CH2CH3, as described in any one of items 1 to 25.

[0185] Section 29.R 14 A compound described in any one of items 1 to 28, wherein the compound is -H.

[0186] Section 30.R 14 A compound described in any one of items 1 to 28, wherein the compound is -CH3.

[0187] Section 31.R 14 However, the compound is -CH2CH3, as described in any one of items 1 to 28.

[0188] Section 32.R 15 A compound described in any one of items 1 to 31, wherein the compound is -H.

[0189] Section 33.R 15 A compound described in any one of items 1 to 31, wherein the compound is -CH3.

[0190] Section 34.R 15 However, the compound is -CH2CH3, as described in any one of items 1 to 31.

[0191] Section 35.R 6 , R 7 , R 22 , R23 , R 29 , and R 30 A compound described in any one of items 1 to 34, wherein none of the above are present, and m, n, and p are each 0.

[0192] Item 36. A compound according to any one of items 1 to 34, wherein m, n, and p are each 1.

[0193] Section 37.R 6 The compound according to claim 36, wherein the compound is -H.

[0194] Section 38.R 6 However, the compound is -CH3 as described in item 36.

[0195] Section 39.R 6 However, the compound is -CH2CH3 as described in item 36.

[0196] Section 40.R 6 However, -CN 、 The compound described in item 36, which is -C(O)N(CH3)2, -CH2C(O)N(CH3)2, -CO2CH3, or -CH2CO2CH3.

[0197] Section 41.R 6 The compound described in item 40, wherein the compound is -CO2CH3 or -CH2CO2CH3.

[0198] Section 42.R 6 The compound described in item 40 or 41, wherein the compound is -CO2CH3.

[0199] Section 43.R 7 A compound described in any one of items 36 to 42, wherein the compound is -H.

[0200] Section 44.R 7 However, the compound is -CH3, as described in any one of items 36 to 42.

[0201] Section 45.R 7 However, the compound is -CH2CH3, as described in any one of items 36 to 42.

[0202] Section 46.R 7 However, -CN 、 A compound according to any one of items 36 to 42, which is -C(O)N(CH3)2, -CH2C(O)N(CH3)2, -CO2CH3, or -CH2CO2CH3.

[0203] Section 47.R 7 The compound described in item 46, wherein the compound is -CO2CH3 or -CH2CO2CH3.

[0204] Section 48.R 7 The compound described in item 46 or 47, wherein the compound is -CO2CH3.

[0205] Section 49.R 22 A compound described in any one of items 36 to 48, wherein the compound is -H.

[0206] Section 50.R 22 However, the compound is -CH3, as described in any one of items 36 to 48.

[0207] Section 51.R 22 However, the compound is -CH2CH3, as described in any one of items 36 to 48.

[0208] Section 52.R 23 A compound described in any one of items 36 to 51, wherein the compound is -H.

[0209] Section 53.R 23 However, the compound is -CH3, as described in any one of items 36 to 51.

[0210] Section 54.R 23 However, the compound is -CH2CH3, as described in any one of items 36 to 51.

[0211] Section 55.R 29 A compound described in any one of items 36 to 54, wherein the compound is -H.

[0212] Section 56.R 29However, the compound is -CH3, as described in any one of items 36 to 54.

[0213] Section 57.R 29 However, the compound is -CH2CH3, as described in any one of items 36 to 54.

[0214] Section 58.R 30 A compound described in any one of items 36 to 57, wherein the compound is -H.

[0215] Section 59.R 30 However, the compound is -CH3, as described in any one of items 36 to 57.

[0216] Section 60.R 30 However, the compound is -CH2CH3, as described in any one of items 36 to 57.

[0217] Section 61.R 4 , R 5 , R 12 , R 13 , R 20 , R 21 , R 31 , R 32 , R 33 , and R 34 However, each is independent of -H, -CN, -CH3, -CH2CH3, -OCH3, -OCH2CH3, -C(O)CH3, -C(O)CH2CH 3、 -CH2C(O)CH3, -CH2COCH2CH 3、 -C(O)2H, -CO2CH3, -CO2CH2CH3, -CH2CO2CH3, -CH2CO2CH2CH3, -NH2, -CH(CH3)NH2, -CH2CH (CH3)NH2, -CH(CH3)CH2NH2, -C(CH3)2NH2, -CH2C(CH3)2NH2, -C(CH3)2CH2NH2, -CH2NH2, -C H2CH2NH2, -CH2CH2CH2NH2, -N(CH3)2, -N(CH2CH3)2, -CH2N(CH3)2, -CH2N(CH2CH3)2, -C(O )N(CH3)2, -C(O)N(CH2CH3)2, -CH2C(O)NH2, -CH2C(O)N(CH3)2, -CH2C(O)N(CH2CH3)2, C4-C12 (hetero)aryl, C2-C8 (hetero)cycloalkyl, A compound described in any one of items 1 to 60, which is TIFF2026062912000053.tif57160.

[0218] Section 62.R 4 , R 5 , R 33 , and R 34 However, each is independent of -H, -CN, -CH3, -CH2CH3, -C(O)CH3, -C(O)CH2CH 3、 -CH2C(O)CH3, -CH2COCH2CH 3、 -CO2H, -CO2CH3, -CO2CH2CH3, -CH2CO2CH3, -CH2CO2CH2CH3, -C(O)N(CH3)2, -C(O)N(CH2CH3)2, -CH2C(O)NH2, -CH2C(O)N(CH3)2, -CH2C(O)N(CH2CH3)2, A compound described in any one of items 1 to 61, which is TIFF2026062912000054.tif43128.

[0219] Section 63.R 4 , R 5 , R 33 , and R 34 A compound according to any one of items 1 to 62, wherein each of the components is independently -H, -CN, -CH3, -CH2CH3, -C(O)CH3, -CH2C(O)CH3, -CO2H, -CO2CH3, -CH2CO2CH3, or -C(O)N(CH3)2.

[0220] Section 64.R 4 A compound described in any one of items 1 to 63, wherein the compound is -H.

[0221] Section 65.R 5 A compound according to any one of items 1 to 64, wherein the compound is -H, -CO2H, or -CO2CH3.

[0222] Item 66.X is CR 33 R 34A compound described in any one of items 1 to 65.

[0223] Section 67.R 33 The compound described in item 66, wherein the compound is -H or -CO2CH3.

[0224] Section 68.R 34 The compounds described in item 66 or 67, wherein the compound is -H, -CN, -CH3, -C(O)CH3, -CO2CH3, -CH2CO2CH3, or -C(O)N(CH3)2.

[0225] Section 69.R 4 , R 5 , R 33 , and R 34 A compound according to any one of items 66 to 68, wherein at least one of them is not H.

[0226] Section 70.R 4 is -H, and R 5 , R 33 , and R 34 A compound described in any one of items 66 to 68, wherein at least one of them is not -H.

[0227] Section 71.R 4 , R 5 , R 33 , and R 34 Each of these is -H, and R 6 and R 7 A compound described in any one of items 66 to 68, wherein at least one of them is not -H.

[0228] Section 72.R 6 and R 7 However, each operates independently as -H, -CH3, -CH2CH3, and -CN. 、 A compound according to any one of items 66-68 or 71, which is -C(O)N(CH3)2, -CH2C(O)N(CH3)2, -C(O)N(CH2CH3)2, -CH2C(O)N(CH2CH3)2, -CO2CH3, or -CH2CO2CH3.

[0229] Section 73.R 6 However, it is -H, and R 7 However, -CN 、 A compound according to any one of items 66-68, 71 or 72, which is -C(O)N(CH3)2, -CH2C(O)N(CH2CH3)2, -CH2C(O)N(CH2CH3)2, -CO2CH3, or -CH2CO2CH3.

[0230] Section 74.R 6 However, it is -H, and R 7 However, the compound is -CO2CH3, as described in item 73.

[0231] Item 75. A compound described in any one of items 1 to 65, wherein X is O.

[0232] Section 76.R 4 and R 5 However, the compound described in item 75 is -H.

[0233] Section 77.R 12 A compound described in any one of items 1 to 61, wherein the compound is -H.

[0234] Section 78.R 13 However, -H, -CH3, -CH2CH3, -CN 、 A compound according to any one of items 1 to 61 or 77, which is -C(O)N(CH3)2, -CH2C(O)N(CH2CH3)2, -CH2C(O)N(CH2CH3)2, -CO2CH3, or -CH2CO2CH3.

[0235] Section 79.R 13 A compound according to any one of items 1-61, 77, or 78, wherein the compound is -H or -CH3.

[0236] Section 80.R 14 A compound described in any one of items 1-61 or 77-79, wherein the compound is -H.

[0237] Section 81.R 14A compound described in any one of items 1-61 or 77-79, wherein the compound is -CH3.

[0238] Section 82.R 16 But -OCH3, -OCH2CH3, -N(CH3)2, -N(CH2CH3)2, A compound described in any one of sections 1-61 or 77-81, which is TIFF2026062912000055.tif43140.

[0239] Section 83.R 16 However, -OCH3, -N(CH3)2, or A compound described in any one of sections 1-61 or 77-82, which is TIFF2026062912000056.tif19128.

[0240] Section 84.R 18 and R 19 However, each is independently -H or -C1-C6 alkyl, and R 20 and R 21 However, each is independent of -H, -CN, -CH3, -CH2CH3, -C(O)CH3, -C(O)CH2CH 3、 -CH2C(O)CH3, -CH2COCH2CH 3、 -C(O)2H, -CO2CH3, -CO2CH2CH3, -CH2CO2CH3, -CH2CO2CH2CH3, -C(O)N(CH3)2, -C(O)N(CH2CH3)2, -CH2C(O)NH2, -CH2C(O)N(CH3)2, -CH2C(O)N(CH2CH3)2, -C4-C 12 (hetero)aryl, -C2-C8 (hetero)cycloalkyl, TIFF2026062912000057.tif43128, and R 24 and R 25However, each is independent of -H, -CN, -C1-C4 alkyl, -C2-C6 (hetero)cycloalkyl, -CH2-O-C1-C4 alkyl, -C(O)-C1-C4 alkyl, -C1-C4 alkyl -C(O)-C1-C4 alkyl, -C(O)-C2-C6 (hetero)cycloalkyl, -C1-C4 alkyl -C(O)-C2-C6 (hetero)cycloalkyl, -CO2H, -CO2-C1-C4 alkyl, -C1-C4 alkyl -CO2-C1-C4 alkyl, -CO2-C2-C6 (hetero)cycloalkyl Kill, -C1-C4 alkylene-CO2-C2-C6(hetero)cycloalkyl, -C1-C4 alkylene-NH2, -C1-C4 alkylene-NH-C1-C4 alkyl, -C1-C4 alkylene-N(C1-C4 alkyl)2, -C(O)NH2, -C1-C4 alkylene-C(O)NH2, -C(O)NH-C1-C4 alkyl, -C(O)N(C1-C4 alkyl)2, -C1-C4 alkylene-C(O)NH-C1-C4 alkyl, -C1-C4 alkylene-C(O)N(C1-C4 alkyl)2, -C4-C 12 A compound according to any one of items 1 to 61, which is (hetero)aryl or -C3-C6(hetero)cycloalkyl.

[0241] Section 85.R 18 and R 19 However, each is independently -H or -C1-C4 alkyl, and R 20 , R 21 , R 24 , and R 25 The compounds described in any one of items 1 to 61 or 84, wherein each is independently -H, -CN, -CH3, -CH2CH3, -C(O)CH3, -CH2C(O)CH3, -CO2CH3, -CH2CO2CH3, -C(O)N(CH3)2, phenyl, cyclopentyl, or cyclohexyl.

[0242] Section 86.R 18 A compound described in any one of items 1-61, 84, or 85, wherein the compound is -H.

[0243] Section 87.R 19A compound described in any one of items 1-61 or 84-86, wherein the compound is -H or -CH3.

[0244] Section 88.R 20 A compound as described in any one of items 1-61 or 84-87, wherein the compound is -H, -CH3, -CH2CH3, -CO2CH3, or phenyl.

[0245] Section 89.R 20 A compound described in any one of items 1-61 or 84-87, wherein the compound is -H.

[0246] Section 90.R 21 A compound as described in any one of items 1-61 or 84-89, wherein the compound is -H, -CH3, -CH2CH3, -CO2CH3, or phenyl.

[0247] Section 91.R 21 A compound as described in any one of items 1-61 or 84-90, wherein the compound is -CH3, -CH2CH3, -CO2CH3, or phenyl.

[0248] Term 92.n is 0, R 22 and R 23 However, the compounds listed in any one of items 1-61 or 84-91 are absent.

[0249] Term 93.n is 1, R 22 and R 23 A compound described in any one of items 1-61 or 84-91, wherein the compound is -H.

[0250] Section 94.R 24 A compound as described in any one of items 1-61 or 84-93, wherein the compound is -H, -CN, -C(O)CH3, -CO2CH3, -CH2CO2CH3, -C(O)N(CH3)2, phenyl, cyclopentyl, or cyclohexyl.

[0251] Section 95.R 24A compound as described in any one of items 1-61 or 84-94, wherein the compound is -H, -CN, -C(O)CH3, -CO2CH3, -CH2CO2CH3, -C(O)N(CH3)2, phenyl, cyclopentyl, or cyclohexyl.

[0252] Section 96.R 25 A compound as described in any one of items 1-61 or 84-95, wherein the compound is -CN, -C(O)CH3, -CO2CH3, -CH2CO2CH3, -C(O)N(CH3)2, phenyl, cyclopentyl, or cyclohexyl.

[0253] Section 97.R 27 and R 28 However, each is independent of -H or -Z-NR 35 R 36 And R 35 and R 36 A compound according to any one of items 1 to 61, wherein each of the members is independently -H, -C1-C6 alkyl, -C1-C6 alkylene-OH, -C1-C6 alkylene-NH2, -C1-C6 alkylene-NH-C1-C6 alkyl, or -C1-C6 alkylene-N-(C1-C6 alkyl)2.

[0254] Section 98.R 27 A compound described in any one of items 1 to 61 or 97, wherein the compound is -H.

[0255] Section 99.R 28 However, -Z-NR 35 R 36 And Z is C1-C4 alkylene, and R 35 and R 36 A compound according to any one of items 1 to 61, 97, or 98, wherein each of the members is independently -H, -C1-C2 alkyl, -C1-C2 alkylene-OH, -C1-C2 alkylene-NH2, -C1-C2 alkylene-NH-C1-C2 alkyl, or -C1-C2 alkylene-N-(C1-C2 alkyl)2.

[0256] Section 100.R 28 However, -Z-NR35 R 36 And R 35 and R 36 The compounds described in any one of items 1-61 or 97-99, wherein each is independently -H or -C1-C2 alkyl.

[0257] Section 101.R 28 A compound described in any one of items 1-61 or 97-100, wherein the compound is -CH(CH3)NH2, -CH(CH3)CH2NH2, -C(CH3)2NH2, -C(CH3)2CH2NH2, -CH2NH2, -N(CH3)2, or -N(CH2CH3)2.

[0258] Section 102.R 28 A compound described in any one of items 1-61 or 97-101, wherein the compound is -C(CH3)2NH2.

[0259] Term 103.p is 0, R 29 and R 30 However, the compounds listed in any one of the items 1-61 or 97-102 are absent.

[0260] Section 104.R 31 and R 32 A compound as described in any one of items 1-61 or 97-103, wherein each of the members is independently -H, -C(O)2H, -CO2CH3, -C(O)N(CH3)2, -C(O)N(CH2CH3)2, -CH2C(O)NH2, -CH2C(O)N(CH3)2, or -CH2C(O)N(CH2CH3)2.

[0261] Section 105.R 31 and R 32 A compound described in any one of items 1-61 or 97-104, wherein each of the following is -H.

[0262] Item 106. A compound according to any one of items 1 to 105, wherein the compound has a boiling point greater than approximately 225°C.

[0263] Item 107. A compound according to any one of items 1 to 106, wherein the compound has a boiling point of at least about 250°C.

[0264] Item 108. A compound according to any one of items 1 to 107, wherein the compound has a boiling point of at least about 260°C.

[0265] Item 109. A compound according to any one of items 1 to 108, wherein the compound has a boiling point of at least about 270°C.

[0266] Item 110. A compound according to any one of items 1 to 109, wherein the compound has a boiling point of at least about 280°C.

[0267] Item 111. A compound according to any one of items 1 to 110, wherein the compound has a gas chromatography retention time longer than diethyl adipate.

[0268] Item 112. The compound described in Item 111, wherein the retention time is at least about 0.5 seconds longer than that of diethyl adipate.

[0269] Item 113. The compound described in item 111 or 112, wherein the retention time is at least about 1.0 second longer than that of diethyl adipate.

[0270] Item 114. A compound according to any one of items 1 to 113, wherein the compound has a gas chromatography retention time longer than hexadecane.

[0271] Item 115. A compound described in any one of items 1 to 114, wherein the retention time is at least about 0.5 seconds longer than that of hexadecane.

[0272] Item 116. A compound according to any one of items 1 to 115, wherein the compound has a gas chromatography retention time longer than methyl palmitate.

[0273] Item 117. A compound according to any one of items 1 to 116, wherein the retention time is at least about 0.5 seconds longer than that of methyl palmitate.

[0274] Item 118. A compound described in any one of items 1 to 117, wherein the compound has a low VOC.

[0275] Item 119. A compound described in any one of items 1 to 118, wherein the compound has lower toxicity than N-methyl-2-pyrrolidione.

[0276] Item 120. A composition comprising a compound of formula I, formula II, formula III, formula IV, or a combination thereof, as described in any one of items 1 to 119.

[0277] Item 121. The composition according to item 120, wherein the compound is substantially free of N-methyl-2-pyrrolidione (NMP).

[0278] Item 122. The composition according to item 121, wherein the compound replaces N-methyl-2-pyrrolidione (NMP) in the composition.

[0279] Item 123. A composition according to any one of items 120 to 122, wherein the composition is a paint or coating, a stripper (e.g., paint, photoresist, furniture, graffiti, wheel, nail polish remover), a cleaner (e.g., oven, surface, floor, automotive, industrial, optical, printed circuit board, or semiconductor), an adhesive / binder / sealant, for leather treatment, for personal care (i.e., commonly used as a surfactant), for screen printing (e.g., lithography, silk), for pharmaceutical formulations, and / or for manufacturing (e.g., electronic equipment such as printed circuit boards, flux removers, or semiconductors, pharmaceuticals, pesticides, petrochemicals, plasticizers, inks).

[0280] Item 124. A method for producing a compound of formula I as described in any one of items 1 to 123, comprising: reacting a nitroalkane with an acrylate reagent to form a nitroalkanoyl reagent; optionally derivatizing the nitroalkanoyl reagent; reducing the nitroacrylate reagent to form an aminoalkanoyl reagent; optionally derivatizing the aminoalkanoyl reagent; and cyclizing the aminoalkanoyl reagent to form a compound of formula Ia. The process involves forming TIFF2026062912000058.tif52128 and alkylating the compound of formula Ia, wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 33 , R 34 A method in which m is defined as any one of terms 1 to 123.

[0281] Item 125. Nitroalkanes are compounds of formula Ib, TIFF2026062912000059.tif27128In formula, R 2 and R 3 The method described in paragraph 124, as defined in any one of paragraphs 1 to 123.

[0282] Item 126. The acrylate reagent is a compound of formula Ic, TIFF2026062912000060.tif41128In formula, R 4 , R 5 , R 34 The method according to item 124 or 125, wherein LG is as defined in any one of items 1 to 125, and LG is a leaving group.

[0283] Section 127. A method for producing a compound of formula I as described in any one of sections 1 to 123, comprising: reacting a nitroalkane with a ketone or aldehyde to form a nitro alcohol; optionally derivatizing the nitro alcohol; reducing the nitro alcohol to form an amino alcohol; optionally derivatizing the amino alcohol; and cyclizing the amino alcohol in the presence of carbon dioxide to form a compound of formula Id. The process involves forming TIFF2026062912000061.tif52128 and alkylating a compound of formula Id, wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 7 A method in which m is defined as any one of terms 1 to 123.

[0284] Item 128. Nitroalkanes are compounds of formula Ib, TIFF2026062912000062.tif27128In formula, R 2 and R 3 The method described in paragraph 127, as defined in any one of paragraphs 1 to 123.

[0285] Item 129. A ketone or aldehyde is a compound of formula Ie. TIFF2026062912000063.tif29128 formula, R 4 and R 5 The method described in paragraph 127 or 128, as defined in any one of paragraphs 1 to 123, 127, or 128.

[0286] Section 130. A method for producing a compound of formula II as described in any one of sections 1 to 123, comprising reacting a nitroalkane with an acrylate reagent to form a nitroalkanoyl reagent, optionally derivatizing the nitroalkanoyl reagent, and reducing the nitroalkanoyl reagent to form a compound of formula IIa. The process involves forming TIFF2026062912000064.tif35128 and alkylating the compound of formula IIa, wherein R 10 , R 11 , R 12 , R 13 , R 14 , R 14 , and R 16 However, the method is as defined in any one of items 1 to 123.

[0287] Item 131. Nitroalkanes are compounds of formula IIb, TIFF2026062912000065.tif27128 in formula, R 10 and R 11 The method described in paragraph 130, as defined in any one of paragraphs 1 to 123.

[0288] Item 132. The acrylate reagent is a compound of formula IIc, TIFF2026062912000066.tif41128In formula, R 12 , R 13 , R 15 , and R 16 The method described in paragraph 130 or 131, as defined in any one of paragraphs 1 to 123.

[0289] Item 133. A method for producing a compound of formula III as described in any one of items 1 to 123, comprising: reducing a nitroalkane to form an alkylhydroxylamine; reacting an alkylhydroxylamine with an aldehyde to form a nitrone; and reacting a nitrone with an alkene.

[0290] Item 134. Nitroalkanes are compounds of formula IIIb, TIFF2026062912000067.tif13128 In formula, R 17 However, the method described in item 133, as defined in any one of items 1 to 123.

[0291] Item 135. Nitron is a compound of formula IIIc, TIFF2026062912000068.tif40128 formula, R 17 , R 18 , and R 19 The method described in paragraph 133 or 134, as defined in any one of paragraphs 1 to 123.

[0292] Item 136. The alkene is a compound of formula IIId, TIFF2026062912000069.tif32128 in formula, R 20 , R 21 , R 24 , and R 25 However, the method described in any one of items 133 to 135, as defined in any one of items 1 to 123.

[0293] Item 137. A method for producing a compound of formula IV as described in any one of items 1 to 123, comprising reacting a nitroalkane with a maleimide to form a nitropyrrolidine-dione, and reducing the nitropyrrolidine-dione to form a compound of formula IV.

[0294] Item 138. Nitropyrrolidine-dione is a compound of formula IVb, TIFF2026062912000070.tif66128 formula, R 26 , R 27 , R 29 , R 30 , R 31 , R 32 , R 35 , R 36 The method described in item 137, wherein Z is defined by any one of items 1 to 123.

[0295] Equivalents While certain embodiments have been illustrated and described, those skilled in the art, after reading the above specification, may make changes, substitutions of equivalents, and other types of modifications to the compounds or salts, pharmaceutical compositions, derivatives, prodrugs, metabolites, tautomers or racemic mixtures thereof described herein. Each of the above embodiments may also include or incorporate any such variations or embodiments disclosed in relation to any or all of the other embodiments.

[0296] This technology is not limited to any particular embodiment described herein, which is intended as a single example of an individual aspect of this technology. Many modifications and variations of this technology can be made without departing from its spirit and scope, as will be apparent to those skilled in the art. Functionally equivalent methods within the scope of this technology will be apparent to those skilled in the art from the foregoing description, in addition to those enumerated herein. Such modifications and variations are intended to fall within the scope of the appended claims. It should be understood that this technology is not limited to any particular method, reagent, compound, composition, labeled compound, or biological system, which may, of course, change. It should also be understood that the terms used herein are merely for describing a particular embodiment and are not intended to limit it. Accordingly, this specification is intended to be considered illustrative only by the breadth, scope, and spirit of this technology as indicated only by the appended claims, the definitions therein, and any equivalent thereof.

[0297] The embodiments described herein by example can be suitably implemented in the absence of any elements or limitations not specifically disclosed herein. Therefore, terms such as “comprising,” “including,” and “containing” are to be read broadly and without limitation. Furthermore, the terms and expressions used herein are for illustrative purposes only, not limitation, and the use of such terms and expressions is not intended to exclude any equivalents of the shown and described features or parts thereof, and it is recognized that various modifications are possible within the scope of the claimed technology. Furthermore, the phrase “essentially consisting of” is to be understood to include several elements specifically cited, and additional elements that do not substantially affect the fundamental and novel features of the claimed technology. The phrase “consisting of” excludes any elements not specified.

[0298] Furthermore, where any feature or aspect of this disclosure is described in relation to the Markush Group, those skilled in the art will recognize that this disclosure is also described in relation to any individual member or subgroup of the members of the Markush Group. Each of the narrower species and subgenera groupings included in the general disclosure also forms part of the invention. This includes the general description of the invention with conditions or negative limitations that exclude any subject from a genus, regardless of whether the deleted material is specifically enumerated herein.

[0299] As will be understood by those skilled in the art, for all purposes, and particularly in terms of providing written explanations, all scopes disclosed herein also encompass all possible subscopes and combinations thereof. Each enumerated scope is well-described and readily apparent as being able to be divided into at least equal halves, thirds, quarters, fifths, tenths, etc. As a non-limiting example, each scope described herein can readily be divided into lower thirds, middle thirds, upper thirds, etc. Furthermore, as will be understood by those skilled in the art, all terms such as “maximum,” “at least,” “greater than,” and “less than” include the enumerated numbers and refer to scopes that can subsequently be divided into subscopes as described above. Finally, as will be understood by those skilled in the art, a scope includes each individual member.

[0300] All publications, patent applications, issued patents, and other documents referenced herein (e.g., periodicals, articles, and / or textbooks) are incorporated herein by reference so that each individual publication, patent application, issued patent, or other document is specifically and individually identified and incorporated in whole by reference. Definitions included in the text incorporated by reference are excluded to the extent that they conflict with the definitions in this disclosure.

[0301] Other embodiments, along with the entire scope of equivalents to which such claims are granted, are described in the following claims.

Claims

1. A compound of formula I, formula II, formula III, or formula IV, During the ceremony, X is O or CR ３３ R ３４ And, R １ 、R ８ 、R ９ 、R １７ 、and R ２６ are each independently, -CH ３ 、-CH ２ CH ３ 、-CH ２ CH ２ CH ３ 、or -CH(CH ３ ) ２ and R ２ , R ３ , R １０ , R １１ , R １４ , and R １５ However, independently of each other, -H and -CH ３ , or -CH ２ CH ３ And, R ６ and R ７ However, each is independent of the others: absent, -H, -CH ３ ien-CH ２ CH ３ , -CN 、 -C(O)N(CH ３ ) ２ ien-CH ２ C(O)N(CH ３ ) ２ , -C(O)N(CH ２ CH ３ ) ２ ien-CH ２ C(O)N(CH ２ CH ３ ) ２ , -CO ２ CH ３ , or -CH ２ CO ２ CH ３ And, R １６ However, -O-C １ -C ８ Alkyl, -O-C ２ -C ８ (hetero)cycloalkyl, -O-C ４ -C １２ (hetero)aryl, -NH ２ , -NH-C １ -C ８ Alkyl, -N(C) １ -C ８ Alkyl) ２ , And, R １８ and R １９ However, each is independent of -H or -C １ -C ８ It is alkyl, R ２２ and R ２３ However, each is independent of the others: absent, -H, or -C. １ -C ８ It is alkyl, R ２４ and R ２５ are each independently, -H, -CN, -C １ -C ８ alkyl, -C ２ -C ８ (hetero)cycloalkyl, -CH ２ -O-C １ -C ８ alkyl, -C(O)-C １ -C ８ alkyl, -C １ -C ８ alkylene-C(O)-C １ -C ８ alkyl, -C(O)-C ２ -C ８ (hetero)cycloalkyl, -C １ -C ８ alkylene-C(O)-C ２ -C ８ (hetero)cycloalkyl, -CO ２ H, -CO ２ -C １ -C ８ alkyl, -C １ -C ８ alkylene-CO ２ -C １ -C ８ alkyl, -CO ２ -C ２ -C ８ (hetero)cycloalkyl, -C １ -C ８ alkylene-CO ２ -C ２ -C ８ (hetero)cycloalkyl, -C １ -C ８ alkylene-NH ２ , -C １ -C ８ alkylene-NH-C １ -C ８ alkyl, -C １ -C ８ alkylene-N(C １ -C ８ alkyl) ２ , -C(O)NH ２ , -C １ -C ８ Alkylene-C(O)NH ２ , -C(O)NH-C １ -C ８ Alkyl, -C(O)N(C １ -C ８ Alkyl) ２ , -C １ -C ８ Alkylene-C(O)NH-C １ -C ８ Alkyl, -C １ -C ８ Alkylene-C(O)N(C) １ -C ８ Alkyl) ２ -(hetero)aryl, -(hetero)cycloalkyl, And, R ４ , R ５ , R １２ , R １３ , R ２０ , R ２１ , R ３１ , R ３２ , R ３３ , and R ３４ However, each is independent of -H, -CN, and -C. １ -C ８ Alkyl, -C ２ -C ８ (hetero)cycloalkyl, -O-C １ -C ８ Alkyl, -CH ２ -O-C １ -C ８ Alkyl, -C(O)-C １ -C ８ Alkyl, -C １ -C ８ Alkylene-C(O)-C １ -C ８ Alkyl, -C(O)-C ３ -C ８ Cycloalkyl, -C １ -C ８ Alkylene-C(O)-C ２ -C ８ (hetero)cycloalkyl, -CO ２ H, -CO ２ -C １ -C ８ Alkyl, -C １ -C ８ Alkylene-CO2 ２ -C １ -C ８ Alkyl, -CO ２ -C ２ -C ８ (hetero)cycloalkyl, -C １ -C ８ Alkylene-CO2 ２ -C ２ -C ８ (hetero)cycloalkyl, -NH ２ , -C １ -C ８ Alkylene-NH ２ , -NH-C １ -C ８ Alkyl, -N(C) １ -C ８ Alkyl) ２ , -C １ -C ８ Alkilen-NHC １ -C ８ Alkyl, -C １ -C ８ Alkylene-N(C) １ -C ８ Alkyl) ２ , -C(O)NH ２ , -C １ -C ８ Alkylene-C(O)NH ２ , -C(O)NH-C １ -C ８ Alkyl, -C(O)N(C １ -C ８ Alkyl) ２ , -C １ -C ８ Alkylene-C(O)NH-C １ -C ８ Alkyl, -C １ -C ８ Alkylene-C(O)N(C) １ -C ８ Alkyl) ２ -(hetero)aryl, -(hetero)cycloalkyl, And, R ２７ and R ２８ However, each is independent of -H or -Z-NR ３５ R ３６ And, Z is C １ -C ８ It is alkylene, R ３５ and R ３６ However, independently of each other, -H and -C １ -C ８ Alkyl, -(hetero)aryl, -(hetero)cycloalkyl, -C １ -C ８ Alkylene-OH, -C １ -C ８ Alkylene-NH ２ , -C １ -C ８ Alkilen-NHC １ -C ８ Alkyl, or -C １ -C ８ Alkylene-N-(C) １ -C ８ Alkyl) ２ And, R ２９ and R ３０ However, each is independent of the others: absent, -H, -CH ３ , or -CH ２ CH ３ And, A compound in which m, n, and p are each independently 0 or 1.

2. R ６ , R ７ , R ２２ , R ２３ , R ２９ , and R ３０ The compound according to claim 1, wherein each of the following is absent, and m, n, and p are each 0.

3. The compound according to any one of claims 1 to 34, wherein m, n, and p are each 1.

4. R ６ However, -H, -CH ３ , or -CH ２ CH ３ The compound according to claim 3.

5. R ６ However, -CN 、 -C(O)N(CH ３ ) ２ ien-CH ２ C(O)N(CH ３ ) ２ , -CO ２ CH ３ , or -CH ２ CO ２ CH ３ The compound according to claim 3.

6. R ７ However, -H, -CH ３ , or -CH ２ CH ３ The compound according to any one of claims 3 to 5.

7. R ７ However, -CN 、 -C(O)N(CH ３ ) ２ ien-CH ２ C(O)N(CH ３ ) ２ , -CO ２ CH ３ , or -CH ２ CO ２ CH ３ The compound according to any one of claims 3 to 5.

8. R ２２ , R ２３ , R ２９ , and R ３０ However, -H, -CH ３ , or -CH ２ CH ３ The compound according to any one of claims 3 to 7.

9. R ４ 、R ５ 、R １２ 、R １３ 、R ２０ 、R ２１ 、R ３１ 、R ３２ 、R ３３ 、and R ３４ are each independently, -H, -CN, -CH ３ 、-CH ２ CH ３ 、-OCH ３ 、-OCH ２ CH ３ 、-C(O)CH ３ 、-C(O)CH ２ CH ３、 -CH ２ C(O)CH ３ 、-CH ２ COCH ２ CH ３、 -C(O) ２ H、-CO ２ CH ３ 、-CO ２ CH ２ [[ID=5৮]]CH ３ 、-CH ２ CO ２ CH[[ID=6५]] ３ 、-CH ２ CO ２ CH ２ CH ３ 、-NH ２ 、-CH(CH ３ )NH ２ 、-CH ２ \nCH(CH ３ )NH ２ 、-CH(CH ３ )CH ２ NH ２ 、-C(CH ３ ) ２ NH ２ [[ID=१८]]、-CH ２ C(CH ３ ) ２ NH ２ 、-C(CH ３ ) ２ CH ２ NH ２ 、-CH ２ NH ２ 、-CH ２ CH ２ NH ２ ien-CH ２ CH ２ CH ２ NH ２ , -N(CH ３ ) ２ , -N(CH ２ CH ３ ) ２ ien-CH ２ N(CH ３ ) ２ ien-CH ２ N(CH ２ CH ３ ) ２ , -C(O)N(CH ３ ) ２ , -C(O)N(CH ２ CH ３ ) ２ ien-CH ２ C(O)NH ２ ien-CH ２ C(O)N(CH ３ ) ２ ien-CH ２ C(O)N(CH ２ CH ３ ) ２ , C ４ -C １２ (hetero)aryl, C ２ -C ８ (hetero)cycloalkyl, The compound according to any one of claims 1 to 8.

10. R ４ 、R ５ 、R ３３ 、and R ３４ are each independently, -H, -CN, -CH ３ 、-CH ２ CH ３ 、-C(O)CH ３ 、-C(O)CH ２ CH ３、 -CH ２ C(O)CH ３ 、-CH ２ COCH ２ CH ３、 -CO ２ H、-CO ２ CH ３ 、-CO ２ CH ２ CH ３ 、-CH ２ CO ２ CH ３ 、-CH ２ CO ２ CH ２ CH ３ 、-C(O)N(CH ３ ) ２ 、-C(O)N(CH ２ CH ３ ) ２ 、-CH ２ C(O)NH ２ 、-CH ２ C(O)N(CH ３ ) ２ 、-CH ２ C(O)N(CH ２ CH ３ ) ２ 、 The compound according to any one of claims 1 to 9.

11. R ４ , R ５ , R ３３ , and R ３４ However, each is independent of -H, -CN, and -CH. ３ ien-CH ２ CH ３ , -C(O)CH ３ ien-CH ２ C(O)CH ３ , -CO ２ H, -CO ２ CH ３ ien-CH ２ CO ２ CH ３ , or -C(O)N(CH ３ ) ２ The compound according to any one of claims 1 to 10.

12. X is CR ３３ R ３４ And R ４ , R ５ , R ３３ , and R ３４ The compound according to any one of claims 1 to 11, wherein at least one of the elements is not H.

13. R ４ is -H, and R ５ , R ３３ , and R ３４ At least one of them is not -H, or R ４ , R ５ , R ３３ , and R ３４ Each of these is -H, and R ６ and R ７ At least one of them is not -H, The compound according to claim 12.

14. The compound according to any one of claims 1 to 11, wherein X is O.

15. R １２ is -H, and R １３ However, -H, -CH ３ ien-CH ２ CH ３ , -CN 、 -C(O)N(CH ３ ) ２ ien-CH ２ C(O)N(CH ３ ) ２ , -C(O)N(CH ２ CH ３ ) ２ ien-CH ２ C(O)N(CH ２ CH ３ ) ２ , -CO ２ CH ３ , or -CH ２ CO ２ CH ３ And R １６ However, -OCH ３ , -N(CH ３ ) ２ ,or The compound according to any one of claims 1 to 9.

16. R １８ and R １９ However, each is independent of -H or -C １ -C ６ It is alkyl, R ２０ and R ２１ However, each is independent of -H, -CN, and -CH. ３ ien-CH ２ CH ３ , -C(O)CH ３ , -C(O)CH ２ CH ３、 -CH ２ C(O)CH ３ ien-CH ２ COCH ２ CH ３、 -C(O) ２ H, -CO ２ CH ３ , -CO ２ CH ２ CH ３ ien-CH ２ CO ２ CH ３ ien-CH ２ CO ２ CH ２ CH ３ , -C(O)N(CH ３ ) ２ , -C(O)N(CH ２ CH ３ ) ２ ien-CH ２ C(O)NH ２ ien-CH ２ C(O)N(CH ３ ) ２ ien-CH ２ C(O)N(CH ２ CH ３ ) ２ , -C ４ -C １２ (hetero)aryl, -C ２ -C ８ (hetero)cycloalkyl, And, R ２４ and R ２５ However, each is independent of -H, -CN, and -C. １ -C ４ Alkyl, -C ２ -C ６ (hetero)cycloalkyl, -CH ２ -O-C １ -C ４ Alkyl, -C(O)-C １ -C ４ Alkyl, -C １ -C ４ Alkylene-C(O)-C １ -C ４ Alkyl, -C(O)-C ２ -C ６ (hetero)cycloalkyl, -C １ -C ４ Alkylene-C(O)-C ２ -C ６ (hetero)cycloalkyl, -CO ２ H, -CO ２ -C １ -C ４ Alkyl, -C １ -C ４ Alkylene-CO2 ２ -C １ -C ４ Alkyl, -CO ２ -C ２ -C ６ (hetero)cycloalkyl, -C １ -C ４ Alkylene-CO2 ２ -C ２ -C ６ (hetero)cycloalkyl, -C １ -C ４ Alkylene-NH ２ , -C １ -C ４ Alkilen-NHC １ -C ４ Alkyl, -C １ -C ４ Alkylene-N(C) １ -C ４ Alkyl) ２ , -C(O)NH ２ , -C １ -C ４ Alkylene-C(O)NH ２ , -C(O)NH-C １ -C ４ Alkyl, -C(O)N(C １ -C ４ Alkyl) ２ , -C １ -C ４ Alkylene-C(O)NH-C １ -C ４ Alkyl, -C １ -C ４ Alkylene-C(O)N(C) １ -C ４ Alkyl) ２ , -C ４ -C １２ (Hetero)aryl, or -C ３ -C ６ The compound according to any one of claims 1 to 9, wherein it is a (hetero)cycloalkyl compound.

17. R ２１ -H, -CH ３ ien-CH ２ CH ３ , -CO ２ CH ３ , or phenyl, where n is 0, R ２２ and R ２３ The compound according to any one of claims 1 to 9 or 16, wherein the compound is absent.

18. R ２４ is -H, -CN, -C(O)CH ３ , -CO ２ CH ３ ien-CH ２ CO ２ CH ３ , -C(O)N(CH ３ ) ２ , phenyl, cyclopentyl, or cyclohexyl, R ２５ is -CN, -C(O)CH ３ , -CO ２ CH ３ ien-CH ２ CO ２ CH ３ , -C(O)N(CH ３ ) ２ The compound according to any one of claims 1 to 9, 16, or 17, wherein the compound is phenyl, cyclopentyl, or cyclohexyl.

19. R ２８ However, -Z-NR ３５ R ３６ And R ３５ and R ３６ However, each is independent of -H or -C １ -C ２ A compound according to any one of claims 1 to 9, wherein it is alkyl.

20. A compound according to any one of claims 1 to 19, having a boiling point exceeding approximately 225°C.

21. A compound according to any one of claims 1 to 20, having a gas chromatography retention time longer than diethyl adipate, hexadecane, methyl palmitate, or a combination of two or more thereof.

22. A compound according to any one of claims 1 to 21, which is low in VOCs.

23. A compound according to any one of claims 1 to 22, having lower toxicity than N-methyl-2-pyrrolidione.

24. A composition comprising a compound of formula I, formula II, formula III, formula IV, or a combination thereof, as described in any one of claims 1 to 23.

25. The composition according to claim 24, which is substantially free of N-methyl-2-pyrrolidione (NMP).

26. The composition according to claim 24 or 25, wherein the composition is a composition known to contain NMP, and the compound replaces the NMP in the composition.

27. The composition according to any one of claims 24 to 26, which is a paint or coating, a stripper (e.g., paints, photoresists, furniture, graffiti, wheels, nail polish remover), a cleaner (e.g., ovens, surfaces, floors, automobiles, industrial, optical, printed circuit boards, or semiconductors), an adhesive / binder / sealant, for leather treatment, for personal care (i.e., commonly used as a surfactant), for screen printing (e.g., lithography, silk), for pharmaceutical formulations, and / or for manufacturing (e.g., electronic equipment such as printed circuit boards, flux removers, or semiconductors, pharmaceuticals, pesticides, petrochemicals, plasticizers, inks).

28. A method for producing a compound of formula I according to any one of claims 1 to 23, The process involves reacting a nitroalkane with an acrylate reagent to form a nitroalkanoyl reagent, Optionally, the nitroalkanoyl reagent may be derivatized, The nitroacrylate reagent is reduced to form an aminoalkanoyl reagent, Optionally, the aminoalkanoyl reagent may be derivatized, The aminoalkanoyl reagent is cyclized to form the compound of formula Ia. To form, This includes alkylating the compound of formula Ia, In the formula, R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ３３ , R ３４ A method wherein m is as defined in any one of claims 1 to 23.

29. A method for producing a compound of formula I according to any one of claims 1 to 23, The reaction of nitroalkanes with ketones or aldehydes to form nitro alcohols, Optionally, the nitro alcohol may be derivatized, The nitro alcohol is reduced to form an amino alcohol, Optionally, the amino alcohol may be derivatized, The amino alcohol is cyclized in the presence of carbon dioxide to form the compound of formula Id. To form, This includes alkylating the compound of formula Id, In the formula, R ２ , R ３ , R ４ , R ５ , R ６ , R ７ A method wherein m is as defined in any one of claims 1 to 23.

30. A method for producing a compound of formula II according to any one of claims 1 to 23, The process involves reacting a nitroalkane with an acrylate reagent to form a nitroalkanoyl reagent, Optionally, the nitroalkanoyl reagent may be derivatized, The nitroalkanoyl reagent is reduced to obtain the compound of formula IIa. To form, This includes alkylating the compound of formula IIa, In the formula, R １０ , R １１ , R １２ , R １３ , R １４ , R １４ , and R １６ A method, as defined in any one of claims 1 to 23.

31. A method for producing a compound of formula III according to any one of claims 1 to 23, The reduction of nitroalkanes to form alkylhydroxylamines, The alkylhydroxylamine and the aldehyde are reacted to form a nitrone, A method comprising reacting the nitrone with an alkene.

32. A method for producing a compound of formula IV according to any one of claims 1 to 23, The reaction of a nitroalkane with maleimide to form a nitropyrrolidinedione, A method comprising reducing the nitropyrrolidinedione to form the compound of formula IV.

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