基于多米诺环的桥接双硫代吡喃[2,3-b]吲哚和非桥接硫代吡喃[2,3-b]吲哚的合成方法

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-09 DOI:10.1021/acs.orglett.5c0065210.1021/acs.orglett.5c00652

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

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引用次数: 0

摘要

揭示了一种新的多米诺骨牌策略，用于构建复杂的桥接双硫代吡喃[2,3-b]吲哚，该策略涉及一个分子的3-甲酰基铬和两个分子的吲哚-2-硫酮，可以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，在温和的反应条件下发生转化。值得注意的是，当这些桥接的双硫代吡喃[2,3-b]吲哚骨架在基本条件下用烷基卤化物处理时，它们被解构成烷基硫代吲哚修饰的硫代吡喃[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。

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

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

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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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.