还原环化法合成2-酰基β-烷基取代2-硝基苯乙烯

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-07-23 DOI:10.1016/j.tet.2025.134838

S.M. Ashikur Rahman , Novruz G. Akhmedov , Ryan M. Ferguson , Björn C.G. Söderberg

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引用次数: 0

摘要

开发了一个合成2-取代3-酰基吲哚的短序列。该序列从2-硝基苯甲醛的维蒂格反应或醛醇反应开始，生成β-酰基-β-烷基取代的2-硝基苯乙烯。苯乙烯通过钯催化、一氧化碳介导的还原环化反应转化为2-取代3-酰基，酰基同时迁移。除了吲哚外，喹啉- n -氧化物和喹啉有时也以较低的分离收率得到。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Synthesis of 2-substituted 3-acylindoles via reductive cyclization – rearrangement of β-acyl β-alkyl-substituted 2-nitrostyrenes

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Synthesis of 2-substituted 3-acylindoles via reductive cyclization – rearrangement of β-acyl β-alkyl-substituted 2-nitrostyrenes

A short synthetic sequence to 2-substituted 3-acylindoles has been developed. The sequence starts with a Wittig or an aldol reaction of 2-nitrobenzaldehydes to give β-acyl-β-alkyl-substituted 2-nitrostyrenes. The styrenes are transformed into 2-substituted 3-acylindoles by a palladium – catalyzed, carbon monoxide – mediated, reductive cyclization with concurrent migration of the acyl group. In addition to indoles, quinoline-N-oxides and quinolines were sometimes obtained in low isolated yields.

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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.