One-pot synthesis of substituted quinolines and 3,3′-(arylmethylene)bis(1H-indoles) via a metal-free polyphosphoric acid-mediated acetylene hydrolysis strategy

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-06-25 DOI:10.1016/j.tet.2025.134801

Nikolai A. Arutiunov, Dinara C. Makieva, Anna M. Zatsepilina, Inna V. Aksenova, Kirill V. Tolstov, Daria A. Shtal, Anastasia A. Korneeva, Elena V. Alexandrova, Alexander V. Aksenov

引用次数: 0

Abstract

Simple one-pot methods for the synthesis of polysubstituted quinolines and 3,3 ′-(arylmethylene) bis (1H-indoles) have been developed using a polyphosphoric acid-mediated alkynes hydrolysis strategy. Sequential addition of substituted alkynes to an o-nitro(o-aminophenyl)carbonyl compound under solvent-free conditions followed by cyclization in polyphosphoric acid afforded 15 diverse quinolines in good to excellent yields. Furthermore, a three-component reaction between aldehydes, acetylenes, and arylhydrazines provided a simple and rapid method for the synthesis of 3,3′-(arylmethylene)bis(1H-indoles) from readily available reagents.

Abstract Image

查看原文本刊更多论文

无金属多磷酸介导乙炔水解一锅法合成取代喹啉和3,3 ' -（芳基亚甲基）双（1h -吲哚）

采用多磷酸介导的炔烃水解策略，建立了一锅法合成多取代喹啉和3,3 ' -（芳基亚甲基）双（1h -吲哚）的简单方法。在无溶剂条件下，将取代炔依次加成至邻硝基（邻氨基苯基）羰基化合物，然后在多磷酸中环化，得到了15种不同的喹啉，收率很高。此外，醛、乙炔和芳基肼之间的三组分反应为从现成的试剂合成3,3 ' -（芳基亚甲基）双（1h -吲哚）提供了一种简单快速的方法。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

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.