One-pot process for synthesizing bicyclic Schiff bases from nitroaromatic hydrocarbons and cyclic aldehydes

By using non-precious metal catalysts and specific polar solvents in the synthesis of nitroaromatics and cyclic aldehydes, the reaction conditions are optimized, and the problems of high catalyst costs and uneven reaction conditions in the prior art are solved, and high-efficiency and low-cost double-rings are achieved. Schiff base synthesis has significantly improved yield and is highly intensive and universal.

CN116514623BActive Publication Date: 2024-12-24NANCHANG UNIV
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Patent Information

Application Number
CN202310492929.X
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2023-05-05
Publication Date
2024-12-24
Estimated Expiration
2043-05-05

AI Technical Summary

Technical Problem

In the prior art, the process of synthesizing bicyclic Schiff base of nitroaromatic hydrocarbons and cyclic aldehydes has problems such as high catalyst cost, mild reaction conditions, many side reactions and low yields, especially in large-scale production and complex molecular synthesis. good.

Method used

Using non-precious metal catalysts, such as nickel phosphide supported by nano-rare earth phosphate, combined with specific polar solvents and mild reaction conditions (85°C, 0.5MPa hydrogen), bicyclic Schiff base is directly synthesized in a closed reaction vessel to optimize the reaction time and stress to improve yield.

Benefits of technology

It has achieved efficient, low-cost and mild conditions, with a yield of 63.8-96.5%, and reduced the safety risks and operational complexity of the process, and has high intensiveness and universality.

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Abstract

The invention discloses a one-pot process for synthesizing bicyclic Schiff bases from nitroaromatics and cyclic aldehydes, belongs to the field of medicine and chemical synthesis technology, and is to provide a convenient and efficient process system and method for directly synthesizing related bicyclic Schiff base medicines or chemical intermediates with nitroaromatics and cyclic aldehyde derivatives. After process development and screening, a process system was invented that uses nickel phosphide supported by nano rare earth phosphate as a cheap catalyst of a specific composition, and directly combines nitroaromatics with benzaldehyde or furfural substrates into corresponding bicyclic Schiff bases at a yield of up to 63.8-96.5% under conditions below 100°C and a hydrogen pressure not higher than 1.0MPa. The process flow of the system is highly intensive, low cost, high and easy to control in terms of operational safety, and high reaction efficiency, which is convenient for promotion and practical application development.
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