Reaction of acylpropargylic alcohols with 1-pyrrolines: A synthetic and quantum-chemical study

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC Tetrahedron Pub Date : 2025-02-28 DOI:10.1016/j.tet.2025.134566

Ludmila A. Oparina, Anton V. Kuzmin, Lyudmila A. Grishchenko, Nikita A. Kolyvanov, Igor’ A. Ushakov, Boris A. Trofimov

引用次数: 0

Abstract

The reactions of acylpropargylic alcohols with 1-pyrrolines (60 °C, 2−3 h) afford the acylethenyltetrahydropyrrolo[2,1-b]oxazoles and furan-3(2H)-ylideneaminoalkanones in 55–76 % and in trace to 12 % yields, respectively. Quantum-chemical calculations (B2PLYP-D3) show that formation of pyrrolo[2,1-b]oxazoles is kinetically more preferable than that of furan-3(2H)-imines, the latter being formed through 1,3(4)-dipole and 2-hydroxypyrrolidine intermediates.

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酰基丙炔醇与1-吡咯啉的反应：合成和量子化学研究

酰基丙炔醇与1-吡咯啉（60℃，2 ~ 3 h）反应，产率为55 ~ 76%，呋喃-3(2H)-酰基四氢吡咯[2,1-b]恶唑和呋喃-3(2H)-酰基胺烷酮产率为12%。量子化学计算（B2PLYP-D3）表明，吡罗[2,1-b]恶唑的形成比呋喃-3(2H)-亚胺的形成更有利，后者通过1,3(4)-偶极子和2-羟基吡啶中间体形成。

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.