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Dihydrofuran heterocyclic compounds and synthesis process thereof

A technology of dihydrofuran and compounds, applied in the field of heterocyclic compounds and their synthesis, which can solve the problems of severe reaction conditions and limited application range

Inactive Publication Date: 2004-09-15
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, many reaction conditions for synthesizing dihydrofuran heterocycles need to be catalyzed by heavy metals or the reaction conditions are relatively severe, which undoubtedly limits its application range.

Method used

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  • Dihydrofuran heterocyclic compounds and synthesis process thereof
  • Dihydrofuran heterocyclic compounds and synthesis process thereof
  • Dihydrofuran heterocyclic compounds and synthesis process thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Reaction of an electron-poor allene with a carbon-oxygen type double center nucleophile in the presence of triphenylphosphine.

[0033] In toluene, add triphenylphosphine (0.2mmol) and corresponding carbon-oxygen double-center nucleophile (1mmol), heat up to 70-80°C for dissolution, then add electron-poor allene (1mmol) toluene solution ( In the synthesis reaction of compound P2, P3, P4, P5, the toluene solution of electron-poor allene is slowly added dropwise to the reaction system with a syringe pump), and the reaction is continued until thin layer chromatography shows that the raw material disappears, the solvent is removed under reduced pressure, and the column Chromatography gave the corresponding dihydrofuran derivative.

[0034] P1: (Reactants: ethyl 2,3-butadienoate, cyclohexanedione)

[0035]

[0036] IR (neat) ν 2947, 1736, 1635, 1404, 1181 cm -1 . 1 H NMR (300MHz, CDCl 3 )δ5.14(m, 1H), 4.14(q, J=7.1Hz, 2H), 2.98(dd, J=14.6, 10.1Hz, 1H), 2.74...

Embodiment 2

[0037]Embodiment 2: In acetonitrile or benzene, add triphenylphosphine (0.2mmol) and corresponding carbon-oxygen type double center nucleophile (1mmol), heat up to 110~120 ℃ for dissolution, then add electron-poor allene ( 1mmol) of toluene solution (in the synthesis reaction of compounds P2 and P3, the toluene solution of electron-poor allene was slowly added dropwise to the reaction system with a syringe pump), and the reaction was continued until thin-layer chromatography showed that the raw materials disappeared, and the solvent was removed under reduced pressure , The corresponding ring dihydrofuran derivatives were obtained by column chromatography.

[0038] P2: (Reactants: 3,4-pentadien-2-one, cyclohexanedione)

[0039]

[0040] IR (neat) ν2948, 1715, 1628, 1406, 1233, 1181cm -1 . 1 H NMR (300MHz, CDCl 3 )δ5.21(m, 1H), 3.06(dd, J=10.5, 14.7Hz, 1H), 2.98(dd, J=17.4, 7.2Hz, 1H), 2.75(dd, J=17.4, 4.8Hz, 1H ), 2.46(dd, J=14.7, 7.2Hz, 1H), 2.42(t, J=6.2Hz, 2H), 2.35(t...

Embodiment 3

[0044] Example 3: Reaction of electron-poor allenes with carbon-oxygen double-center nucleophiles in the presence of tributylphosphine.

[0045] The reaction process and post-treatment were the same as in Example 1. The toluene solution of electron-poor allene was slowly dripped into the reaction system with a syringe pump, and the catalyst was changed to tributylphosphine.

[0046] P4: (Reactants: 3,4-pentadien-2-one, acetylacetone)

[0047]

[0048] IR (neat) ν 2926, 1716, 1670, 1618, 1602, 1324, 1228cm -1 . 1 H NMR (300MHz, CDCl 3 )δ5.02(m, 1H), 3.17(dd, J=11.5, 14.3Hz, 1H), 2.96(dd, J=17.0, 7.1Hz, 1H), 2.71(dd, J=17.0, 6.2Hz, 1H ), 2.57 (dd, J=14.3, 7.5Hz, 1H), 2.21 (s, 3H), 2.19 (s, 3H), 2.17 (s, 3H). MS (m / z) 182 (M + ), 125, 109, 97, 43(100), 41. Elemental Analysis C 10 h 14 o 3 : Calculated C, 68.02; H, 7.27. Found C, 64.04; H, 7.54.

[0049] P5: (Reactants: 3,4-pentadien-2-one, ethyl acetoacetate)

[0050]

[0051] Mp 43-44℃.IR(KBr)ν2982, 1716, 1698, 16...

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Abstract

A dihydrofuran compound is prepared through the reaction of the electron-deficiency diene and alkyne with the nucleophilic reagent with dual nucleophilic sites. Its advantages are simple preparing process and high yield.

Description

technical field [0001] The invention relates to a heterocyclic compound and a synthesis method thereof, in particular to a dihydrofuran compound and a synthesis method thereof. Background technique [0002] Dihydrofuran organic heterocyclic compounds are widely used in organic synthesis, pesticides, medicine and other fields, and are important structural units of chemical products in these fields. These structural units are also included in many molecules with physiological activity. For example, compound 1 is an enzyme inhibitor (Lee, D.-S.; Lee, S.-H.; Nah, J.-G.; Hong, S.-D. Biosci. Biotechnol. Biochem. 1999, 63, 2236), Compound 2 is an ion channel blocker involved in immune function (Butenschn, I; Mller K; Hnsel, W.J.Med.Chem.2001, 44, 1249). Compound 3 is a substance with anti-platelet aggregation effect isolated from natural products (Jong, T.T.; Wu, T.S. Phytochemistry(s) 1989, 28, 245). Compound 4 is a natural product with anthelmintic effect (Kato, S.; Shibaya...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/12C07D307/94
Inventor 陆琤陆熙炎
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI