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Preparation method of multi-substituted furan compound

A technology for polysubstituted furans and compounds is applied in the field of preparation of polysubstituted furans, and achieves the effects of strong designability, easy availability and easy operation.

Active Publication Date: 2014-12-24
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, this method has some limitations. For example, the starting substrate needs to be synthesized in multiple steps in advance; for some substrates containing sensitive groups, anhydrous and oxygen-free experimental operations are required.

Method used

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  • Preparation method of multi-substituted furan compound
  • Preparation method of multi-substituted furan compound
  • Preparation method of multi-substituted furan compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～7

[0037] Add metal salt, alkyl substituted ketone (II), α, β-unsaturated carboxylic acid (III) and 2ml of organic solvent into a 35ml Schlenk tube according to the raw material ratio in Table 1, mix and stir evenly, and follow the reaction in Table 2 After the conditional reaction is completed, filter, mix the sample with silica gel, and purify by column chromatography (petroleum ether as the eluent) to obtain the corresponding multi-substituted furan compound (I). The reaction process is shown in the following formula:

[0038]

[0039] The raw material proportioning of table 1 embodiment 1~7

[0040]

[0041] The reaction conditions and the result of table 2 embodiment 1~7

[0042]

[0043]

[0044] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, Me is methyl, Ph is phenyl, n-C 4 h 9 is n-butyl, 4MeO-Ph is p-methoxyphenyl, 1-naphtyl is naphthyl, DMF is N,N-dimethylformamide, DMA is N,N-dimethylacetamide, (I- 1)~(I-7) For the specif...

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Abstract

The invention discloses a preparation method of a multi-substituted furan compound. The preparation method comprises the following steps of: adding metal salt, alkyl substituted ketone and Alpha, Beta-unsaturated carboxylic acid to an organic solvent; heating to reach 120 to 150 DEG C for reacting completely; and then post-processing to obtain the multi-substituted furan compound, wherein the metal salt consists of cuprous salt and cupric salt. The preparation method used for the multi-substituted furan compound, provided by the invention, is easy to operate, simple and convenient in post-processing, high in substrate designability, capable of designing and synthesizing compounds with required structures according to the actual demand, and relatively high in practicability.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of multi-substituted furan compounds. Background technique [0002] As an important five-membered oxygen-containing heterocyclic ring, furan compounds widely exist in natural products and molecular structures with biological activity (Tetrahedron1998, 54, 1955). Many drug molecules contain furan structure skeletons, for example, dantrolene is an important Its sodium salt is a muscle relaxant that directly acts on skeletal muscle; furazolidone is a kind of fungicide with a wide bactericidal spectrum: [0003] [0004] Multi-substituted furan compounds are important intermediates in synthetic chemistry (Chem. Rev. 1985, 86, 795). For example, polysubstituted furans can be used to prepare o-acetamidobenzoic acids by using the intermolecular Diels-Alder reaction: [0005] [0006] In addition to the classic cyclocondensation reaction of dicarbonyl compoun...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/36C07D307/42
Inventor 张玉红杨誉竹姚金忠
Owner ZHEJIANG UNIV