Method for synthesizing rutaecarpin and derivatives thereof through two-step tandem hydrogen borrowing reaction

The synthesis of evodiamine and its derivatives via a two-step tandem hydrogen-borrowing reaction solves the problems of long reaction time, high temperature, and cumbersome steps in existing methods, realizing an efficient and green synthetic route with water as a byproduct, readily available raw materials, and a simple synthetic route.

CN121085918APending Publication Date: 2025-12-09GUILIN UNIVERSITY OF TECHNOLOGY
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Patent Information

Application Number
CN202511220022.3
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2025-08-28
Publication Date
2025-12-09

AI Technical Summary

Technical Problem

Existing methods for the chemical synthesis of evodiamine and its derivatives suffer from drawbacks such as long reaction times, high temperatures, cumbersome steps, or simple derivative structures, and lack green and simple synthetic methods.

Method used

A two-step tandem hydrogen-borrowing reaction strategy was adopted, using ethylene glycol as the alkylating agent. 2-aminobenzamide reacted with 1H-indole-2-carboxaldehyde under the catalysis of p-toluenesulfonic acid to generate an intermediate, which was then oxidized with 2,3-dichloro-5,6-dicyanobenzoquinone. Finally, hydrogen-borrowing reaction was carried out with ethylene glycol under the iridium catalyst to complete the alkylation and synthesis of the target compound.

Benefits of technology

The efficient and green synthesis of evodiamine and its derivatives was achieved, with water as the only byproduct. The raw materials are readily available, the synthetic route is simple, and it is atom-economical.

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Abstract

The rutaecarpin and the derivative thereof are synthesized by using a hydrogen borrowing reaction strategy. In an experiment, ethylene glycol is used as a solvent and an alkylating reagent, and the ethylene glycol and a substrate are subjected to a heating reaction in the presence of an iridium-based catalyst under an alkaline condition to prepare a target product. In the reaction process, two hydroxyl groups in the ethylene glycol are respectively and successively converted into formyl groups, and then a nucleophilic addition reaction of aldehyde is carried out; and the alkylation reaction is completed through the steps of dehydration, reduction and the like. In the whole reaction process, hydrogen and other reducing agents do not need to be additionally added, and only water serves as a byproduct. Therefore, from the perspective of synthetic chemistry and environmental protection, the hydrogen borrowing reaction method has the characteristics of high efficiency and greenness, and has a wide application prospect.
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