Dithiane-Enabled Divergent Ring Rearrangements for the Construction of Sulfur-Containing Semisaturated Fused Pyridines and Pyrroles

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-01 DOI:10.1021/acs.orglett.6c03956

Xiaomeng Gong, Guohong Tang, Yingying Xue, Rui-Peng Li, Shouchu Tang

引用次数: 0

Abstract

Sulfur-containing semisaturated N-heterocycles represent valuable three-dimensional drug-relevant scaffolds, yet general divergent synthetic approaches remain scarce. Herein, we report a metal-free cis-selective [3 + 2] cycloaddition between alkynyl 1,3-dithianes and 2H-azirines to construct strain-encoded bicyclic aziridine intermediates. The 1,3-dithiane unit functions as a sulfur shuttle that enables two reagent-controlled rearrangement pathways: Brønsted-acid-mediated ring expansion through 1,2-sulfur migration affords sulfur-functionalized semisaturated fused pyridines, whereas oxidative Lewis-acid-promoted ring contraction furnishes sulfur-functionalized semisaturated fused pyrroles.

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含硫半饱和熔融吡啶和吡咯的分散环重排

含硫半饱和n -杂环化合物是有价值的三维药物相关支架，但一般的合成方法仍然很少。在本文中，我们报道了在炔基1,3-二硫烷和2h -氮嘧啶之间无金属顺式选择性[3 + 2]环加成，以构建菌株编码的双环氮嘧啶中间体。1,3-二thiane单元作为硫穿梭体，实现了两种试剂控制的重排途径：br ønsted酸通过1,2-硫迁移介导的环扩张提供了硫功能化的半饱和熔融吡啶，而lewis酸促进的氧化环收缩提供了硫功能化的半饱和熔融吡咯。

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.