Synthesis of Pyrazoline-Derived N-Vinyl Nitrones through An Unexpected Selective [3+2] Cycloaddition

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-03-04 DOI:10.1039/d4qo02317j

Pei-Wen Qiu, Li-Bing Yan, Li-Fen Ning, Chun-Hua Chen, Hong-Yan Bi, Dong-Liang Mo

引用次数: 0

Abstract

A variety of pyrazoline-derived N-vinyl nitrones were prepared in moderate to good yields with high diastereoselectivity through base-promoted regioselective [3+2] cycloaddition of N-vinyl chalcone nitrones with hydrazonoyl chlorides under mild reaction conditions. The mechanistic studies revealed that the E-isomer of N-vinyl nitrones facilitated to be converted into pyrazoline-derived N-vinyl nitrones than Z-isomer. The present method features broad substrate scope, good functional group tolerance, high regioselectivity and diastereoselectivity, novel type of N-vinyl nitrones, and N-vinyl nitrones served as dipolarophiles.

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.