Facile synthesis of spiro-heterocycles through one-pot multicomponent [3 + 3] cross 1,3-dipolar cycloaddition reactions

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2024-10-26 DOI:10.1016/j.tet.2024.134328

Guo-Yang Ma , Ya-Fei Li , Qing Xu , Yue-Yao Ma , Ya-Wen Li , Guo-Qiang Gong , Ning Zhang , Tan Dang , Kai-Kai Wang

引用次数: 0

Abstract

A three-component 1,3-dipolar cycloaddition reaction involving ninhydrin, proline, and nitrile imines, which are generated in situ from hydrazonoyl chlorides, has been developed. This transformation can be conceptualized as a cross-1,3-dipolar cycloaddition reaction between two distinct ylides, proceeding via a [3 + 3] annulation pathway. This approach offers a swift route to a diverse array of novel and structurally intricate spiro-multiheterocyclic skeletons, achieving good yields ranging from 80 % to 94 %. Furthermore, the chemical structure of a representative product has been rigorously confirmed via X-ray diffraction analysis.

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通过单锅多组分[3 + 3]交叉 1,3-二极环加成反应轻松合成螺环杂环

我们开发了一种涉及茚三酮、脯氨酸和腈亚胺的三组分 1,3-二极环加成反应，腈亚胺是由肼酰氯原位生成的。这种转化可以概念化为两种不同酰化物之间的交叉-1,3-双极环加成反应，通过[3 + 3]环化途径进行。这种方法提供了一条通向一系列结构复杂的新型螺多杂环骨架的捷径，可获得 80% 至 94% 的良好产率。此外，一种代表性产品的化学结构已通过 X 射线衍射分析得到严格确认。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.