Alkenyl amide triazole compound and synthetic method thereof

Abstract

The invention discloses an alkenyl amide triazole compound and a synthetic method thereof. The compound has the following structural formula (see the formula in the description). According to the synthetic method, alkyl or aryl azide, various kinds of amine and various substituted 5-halogeno-2-furfuryl alcohol compounds are used as starting raw materials, and a 1,2,3-triazole and alkenyl amide conjugated skeleton structure of (Z)-configuration is generated through a [3+2]-cycloaddition, furan ring opening and amidating series reaction accelerated by lewis acid. The synthetic method is easy to operate, the used reagent is the low-cost lewis acid, the substrate is wide in application range and capable of being used for synthesizing a series of complex alkenyl amide triazole compounds substituted by functional groups highly, and step economy, product structural diversity and (Z)-configuration stereospecificity are high.

Description

technical field [0001] The invention relates to a class of enamide triazole compounds and a synthesis method thereof. Background technique [0002] For drug discovery and the development of cell signaling molecular probes, rapid and reliable synthesis of heterocyclic compounds has become one of the core parts in these fields. 1,2,3-triazoles exhibit unique advantages, and compounds with this type of structure have been proven to have a broad spectrum of biological activities. They have been widely used in organic synthesis, biochemistry and materials science. Among them, the enamide triazole skeleton structure represents an important class of small molecular compounds. Due to its high biocompatibility, this kind of backbone has been studied to have an inhibitory effect on histone deacetylase (HDAC). Histone deacetylase inhibitors inhibit the proliferation of tumor cells and induce cell differentiation and (or) apoptosis by increasing the degree of acetylation of intracell...

AI Technical Summary

Problems solved by technology

[0003] At present, the methods for the synthesis of triazole skeletons mainly focus on: 1,3-dipole azide-alkyne cycloaddition (AAC), but the multi-step synthesis of reaction precursors limits its further application; the strained alkyne Participated cycloaddition has become a very important synthetic tool and has been widely used; alkynes conjugated with electron-withdrawing functional groups can also synthesize triazoles under mild conditions; enamines or enols conjugated with carbonyl groups can also be combined with azide Synthesis of triazoles from compounds via cycloaddition / elimination reactions

However, it is clear that all of these reported enamide triazole compounds require a very tedious multi-step synthesis without a simple and straightforward approach using inexpensive and readily available compounds as starting materials.

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