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

IF 2.1 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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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.