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A kind of synthetic method of tetrahydroisoindole-1,3-dione derivative

A technology of tetrahydroisoindole and synthesis method is applied in the field of tetrahydroisoindole-1 and achieves the effects of mild reaction conditions, simple operation and low cost

Active Publication Date: 2020-09-08
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, electron-rich indole ring derivatives with N-substituted maleimides in 2,3-dichloro-5,6-dicyano-p-benzoquinone or 2,3,5,6-tetrachloro-p- The DHDA reaction under the action of benzoquinone has been reported, but other types of substrates have not been reported to synthesize tetrahydroisoindole 1,3-dione derivatives by this strategy

Method used

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  • A kind of synthetic method of tetrahydroisoindole-1,3-dione derivative
  • A kind of synthetic method of tetrahydroisoindole-1,3-dione derivative
  • A kind of synthetic method of tetrahydroisoindole-1,3-dione derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0024] 6-Methyl-2-(4-nitrophenyl)-4-phenyl-3a,4,7,7a-1H-tetrahydroisoindole-1,3(2H)-dione(±)- Synthesis of ((3aR, 4R, 7aS)-6-methyl-2-(4-nitrophenyl)-4-phenyl-3a, 4, 7, 7a-tetrahydro-1H-isoindole-1, 3(2H)-dione)

[0025] With (3-Methyl-but-2-enyl)-benzene (compound 1a), N-(4-nitrophenyl) maleimide (compound 2) as raw material and in 2,3-dichloro-5 , The reaction under the oxidation of 6-dicyano-p-benzoquinone produces 6-methyl-2-(4-nitrophenyl)-4-phenyl-3a, 4,7,7a-1H-tetrahydroisoindole -1,3(2H)-diketone (compound 3a), its chemical reaction formula is:

[0026]

[0027] The method is specifically:

[0028] Under the protection of inert gas (nitrogen or argon), (3-Methyl-but-2-enyl)-benzene (0.40mmol), 2,3-dichloro-5,6-dicyano-p-benzoquinone (0.3mmol ), N-(4-nitrophenyl)maleimide (0.20mmol) was added to a Schlenk bottle, nitrogen was replaced three times, 2mL of chlorobenzene was added (calcium hydride was distilled to remove water), heated to 110°C for 60h, TLC plate mo...

Embodiment 2

[0034]6-Methyl-2-(4-nitrophenyl)-4-(2-fluorophenyl)-3a,4,7,7a-1H-tetrahydroisoindole-1,3(2H)-di Ketone (±)-((3aR,4R,7aS)-4-(2-fluorophenyl)-6-methyl-2-(4-nitrophenyl)-3a,4,7,7a-tetrahydro-1H-isoindole-1, Synthesis of 3(2H)-dione)

[0035] With 1-Fluoro-2-(3-methyl-but-2-enyl)-benzene (compound 1b), N-(4-nitrophenyl) maleimide (compound 2a) as raw material and in 2, 6-Methyl-2-(4-nitrophenyl)-4-(2-fluorophenyl-3a,4,7 was prepared by oxidation reaction of 3-dichloro-5,6-dicyano-p-benzoquinone , 7a-1H-tetrahydroisoindole-1,3(2H)-dione (compound 3b), its chemical reaction formula is:

[0036]

[0037] The method is specifically:

[0038] Under the protection of inert gas (nitrogen or argon), 1-Fluoro-2-(3-methyl-but-2-enyl)-benzene (0.30mmol), 2,3-dichloro-5,6-dicyano Add p-benzoquinone (0.2mmol), N-(4-nitrophenyl)maleimide (0.20mmol) into a Schlenk bottle, replace nitrogen three times, add 2mL chlorobenzene (calcium hydride distilled to remove water), heat to Reacted at 1...

Embodiment 3

[0044] 6-methyl-2-(4-nitrophenyl)-4-(2-chlorophenyl)-3a,4,7,7a-1H-tetrahydroisoindole-1,3(2H)-di Ketone (±)-((3aR,4R,7aS)-4-(2-chlorophenyl)-6-methyl-2-(4-nitrophenyl)-3a,4,7,7a-tetrahydro-1H-isoindole-1, Synthesis of 3(2H)-dione)

[0045] With 1-Chloro-2-(3-methyl-but-2-enyl)-benzene (compound 1c), N-(4-nitrophenyl) maleimide (compound 2) as raw material and in 2, The reaction under the oxidation of 3-dichloro-5,6-dicyano-p-benzoquinone produced 6-methyl-2-(4-nitrophenyl)-4-(2-chlorophenyl)-3a,4, 7,7a-1H-tetrahydroisoindole-1,3(2H)-dione (compound 3c), its chemical reaction formula is:

[0046]

[0047]

[0048] The method is specifically:

[0049] Under the protection of inert gas (nitrogen or argon), 1-Chloro-2-(3-methyl-but-2-enyl)-benzene (0.50mmol), 2,3-dichloro-5,6-dicyano Add p-benzoquinone (0.4mmol), N-(4-nitrophenyl)maleimide (0.20mmol) into a Schlenk bottle, replace nitrogen three times, add 2mL of chlorobenzene (calcium hydride distilled to remove water),...

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Abstract

The invention discloses a synthesis method of tetrahydroisoindole-1,3-dione derivatives. The method uses isopentenyl benzene compounds with the molecular formula and N-substituted maleimides with the molecular formula It is used as a raw material and reacted under the action of an oxidizing agent to obtain a tetrahydroisoindole 1,3-dione derivative with the molecular formula. In the present invention, the isopentenylbenzene compound reacts with N-substituted maleimide under the oxidation of p-benzoquinone compound to undergo DHDA reaction, and directly and efficiently prepares tetrahydroisoindole 1,3 with endo configuration -diketone derivatives, the preparation process is simple, the reaction conditions are mild, and the reaction is efficient, and only one step reaction can directly build two C-C bonds; the raw materials used in the present invention are low in cost and do not need to be prepared in advance into co- Conjugated diene, oxidant p-benzoquinone compound is easy to prepare and has no pollution, thus realizing the purpose of green and high efficiency.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a synthesis method of tetrahydroisoindole-1,3-dione derivatives. Background technique [0002] Tetrahydroisoindole-1,3-dione derivatives are an important class of organic synthesis intermediates, and their skeletons widely exist in biologically active natural products and synthetic compounds. Tetrahydroisoindole-1,3-dione derivatives also have flexible derivatization capabilities, and can be transformed into a variety of similar skeleton molecules with drug and pesticide activities, such as glyphosate, indobuprofen, etc. There are only a few reactions, such compounds are synthesized by the Diels-Alder reaction of conjugated dienes and their derivatives under noble metal catalyzed conditions with N-substituted maleimides. However, some conjugated dienes are unstable and require pre-preparation, which limits the synthesis of such compounds. So far, there is ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/48
CPCC07D209/48
Inventor 雷依波周岭陈洁许文磊
Owner NORTHWEST UNIV
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