烷基异氰酸酯、二烷基丁-2-炔酸酯和2-芳基-1,3-茚二酮三组分反应的分子多样性

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-07-25 DOI:10.1016/j.tet.2025.134853

Shao-Cong Zhan, Li Huang, Jing Sun, Chao-Guo Yan

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引用次数: 0

摘要

烷基异氰酸酯、二烷基丁-2-炔酸酯和2-芳基-1,3-茚二酮的三组分反应显示出非常有趣的分子多样性。三组分反应在回流乙腈中得到功能化的螺[呋喃-2,1 ' -茚]衍生物。另一方面，三组分反应在回流乙醇中得到功能化环五[b]萘衍生物。此外，烷基异氰酸酯、二烷基丁-2-炔酸酯和5-芳基烯-N，N ' -二甲基巴比妥酸的类似三组分反应可得到功能化的重氮斯匹罗[4.5]十二-1,3-二烯-1,2-二羧酸酯，收率令人满意。提出了一种合理的反应机制，包括Huisgen的1,4偶极子原位反应和顺序环化反应，以解释不同多环化合物的形成。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Molecular diversity of three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 2-arylidene-1,3-indanediones

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Molecular diversity of three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 2-arylidene-1,3-indanediones

The three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 2-arylidene-1,3-indanediones showed very interesting molecular diversity. The three-component reaction in refluxing acetonitrile afforded functionalized spiro[furan-2,1′-indene] derivatives. On the other hand, the three-component reaction in refluxing ethanol gave functionalized cyclopenta[b]naphthalene derivatives. In addition, the similar three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 5-arylidene-N,N′-dimethylbarbituric acids resulted in functionalized diazaspiro[4.5]deca-1,3-diene-1,2-dicarboxylates in satisfactory yields. A plausible reaction mechanism including in situ of Huisgen's 1,4-dipole, and sequential annulation reaction was proposed to explain the formation of the different polycyclic compounds.

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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.