Indole derivatives obtained by converting quinoline nitrogen-oxides and a method for synthesizing the same

A one-pot method for converting the quinoline skeleton to the indole skeleton was achieved through a cyclization rearrangement reaction catalyzed by diphenyl phosphate and the removal of the side chain by trichloroacetic acid. This method solves the inapplicability and environmental problems of existing quinoline skeleton conversion methods and provides new ideas for a wide range of product structures and drug molecule design.

CN119661415BActive Publication Date: 2025-12-05SHANGHAI JIAOTONG UNIV
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Patent Information

Application Number
CN202411760543.3
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2024-12-03
Publication Date
2025-12-05
Estimated Expiration
2044-12-03

AI Technical Summary

Technical Problem

Existing technologies lack universal and environmentally unfriendly methods for directly editing molecular skeletons, especially the conversion of quinoline skeletons to indole skeletons. The product structures are narrow and require complex reaction conditions and metal involvement.

Method used

The cyclization rearrangement reaction of quinoline oxynitride and dimethyl butynedioate was catalyzed by diphenyl phosphate and the side chain was removed by trichloroacetic acid. The transformation of the quinoline skeleton to the indole skeleton was achieved in a one-pot process under mild conditions, avoiding complex de novo synthesis and metal involvement.

Benefits of technology

This method achieves efficient conversion of the quinoline skeleton to the indole skeleton, with a wide range of product structures, mild reaction conditions, simple operation, low cost, atom economy and environmental friendliness, and is suitable for drug molecule design and optimization.

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Abstract

The application relates to an indole derivative obtained by converting quinoline nitrogen-oxide and a synthesis method of the indole derivative, the chemical structural formula of the derivative is shown as formula 2; the synthesis method is as follows: quinoline nitrogen-oxide, dimethyl acetylene dicarboxylate and water are used as reaction raw materials and are added into 1,2-dichloroethane solvent, a first heating stirring reaction is carried out under the catalysis of diphenyl phosphate, after TLC monitoring shows that the conversion of quinoline nitrogen-oxide of formula 1 compound is complete, trichloroacetic acid and molecular sieve dehydrating agent are added, a second heating stirring reaction is carried out, the reaction is monitored until complete through TLC, the solvent is evaporated, and then purification is carried out to obtain the indole derivative. The method has the advantages of high atom economy, mild reaction condition, green, low cost, high conversion rate and the like, meanwhile, the method is a carbon recombination strategy for directly editing a molecular skeleton, can provide a new idea for late-stage design and optimization of a drug molecule, and can accelerate the drug discovery and development process, and has good theoretical value and application prospect.
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