Domino-Annulation-Based Approach to Synthesize Bridged Bis-thiopyrano[2,3-b]indoles and Unbridged Thiopyrano[2,3-b]indoles

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-09 DOI:10.1021/acs.orglett.5c00652

Yan-Hui Fu, Chun Zhang, Wei Xu, Wenting Fu, Wenjun Zhang, Kang Zhou, Hongbin Zhai, Taimin Wang, Bin Cheng

引用次数: 0

Abstract

A novel domino strategy for the construction of intricate bridged bis-thiopyrano[2,3-b]indoles was disclosed, which involved one molecule of 3-formylchromones and two molecules of indoline-2-thiones, enabling the formation of four new bonds in a single operation. The transformation occurred under mild reaction conditions, facilitated by the synergistic action of the base NaHCO₃ and the catalytic acid ZnCl₂. Notably, when these bridged bis-thiopyrano[2,3-b]indole skeletons were treated with alkyl halides under basic conditions, they underwent deconstruction to yield alkylthio-substituted indole-decorated thiopyrano[2,3-b]indoles.

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该研究揭示了一种构建复杂桥式双硫吡喃并[2,3-b]吲哚的新型多米诺战略，其中涉及一分子 3-甲酰基色素和两分子吲哚啉-2-硫酮，从而能够在一次操作中形成四个新键。在碱 NaHCO3 和催化酸 ZnCl2 的协同作用下，转化在温和的反应条件下进行。值得注意的是，当这些桥接的双硫吡喃并[2,3-b]吲哚骨架在碱性条件下用烷基卤化物处理时，它们会发生解构，生成烷硫基取代的吲哚装饰的硫吡喃并[2,3-b]吲哚。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.