One‐Pot Tandem [4 + 4] Annulation of 2‐Fluoro‐N‐arylbenzenesulfonamides with 2‐Methylidenetrimethylene Carbonates: Access to Functionalized Benzoxathiazocines

IF 4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-10-06 DOI:10.1002/adsc.70155

Yuming Li, Yan Gou, Shanling Hou, Yong Gao, Yaqi Xuan, Zhi Fan

引用次数: 0

Abstract

In this article, a Pd(0)/ NaH‐mediated [4 + 4] cascade annulation reaction of 2‐fluoro‐N‐arylbenzenesulfonamides and 2‐methylidenetrimethylene carbonate is developed, providing the benzo[b][1,4,5]oxathiazocine‐1,1‐dioxides in generally excellent yields (71−95%), and some of the enantioenriched products featuring C–N axial chirality are also achieved (up to 88% yield and 60% ee) under mild conditions. Moreover, the synthesized compounds exhibit promising anticancer activity against human cancer cell lines Hela (cervical cancer), highlighting their potential applications for drug screening.

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2 -氟- N -芳基苯磺酰胺与2 -甲基三亚甲基碳酸酯的一锅串联[4 + 4]环化：获得功能化苯并恶噻嗪

在本文中，开发了Pd(0)/ NaH介导的2 -氟- N -芳基苯磺酰胺和2 -甲基二亚甲基碳酸酯的[4 + 4]级联环反应，提供了苯并[b][1,4,5]恶唑嗪- 1,1 -二氧化物，收率一般很好（71 - 95%），并且在温和的条件下也获得了一些具有C-N轴向手性的对映体富集产物（收率高达88%，ee为60%）。此外，合成的化合物对人宫颈癌Hela细胞系具有良好的抗肿瘤活性，在药物筛选方面具有潜在的应用前景。

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

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.