邻炔基苯基异硫氰酸酯铜催化串联环化选择性构建2,4-双硫代喹啉

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-02-07 DOI:10.1021/acs.joc.4c0199110.1021/acs.joc.4c01991

Guojian Fang, Xuan Wu, Xiaoyan Sang, Han Wang and Wenyan Hao*,

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引用次数: 0

摘要

选择性合成多取代喹啉已被认为是一个重要但极具挑战性的转变。在本研究中，利用廉价且易得的硫化钠（Na2S）作为硫源，通过铜（II）促进邻炔基苯基异硫氰酸酯的串联环加成，开发了一种高效合成2,4-双硫代喹啉的方法。这种转化可以在一锅反应中通过形成C-C和C-S键直接合成2,4-双（硫代喹啉）杂环，对各种官能团具有良好的耐受性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Selective Construction of 2,4-Bisthioquinolines via Copper-Catalyzed Tandem Cyclization from o-Alkynylphenyl Isothiocyanates

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Selective Construction of 2,4-Bisthioquinolines via Copper-Catalyzed Tandem Cyclization from o-Alkynylphenyl Isothiocyanates

The selective synthesis of polysubstituted quinoline has been recognized as an important but highly challenging transformation. In this study, a highly efficient method for the synthesis of 2,4-bisthioquinolines has been developed through a copper(II)-promoted tandem cycloaddition of o-alkynylphenyl isothiocyanates, utilizing inexpensive and readily available sodium sulfide (Na₂S) as the sulfur source. This transformation enables the direct synthesis of 2,4-bis(thioquinoline) heterocycles via the formation of C–C and C–S bonds in a one-pot reaction, demonstrating excellent tolerance for various functional groups.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.