Trimethylsilyl Triflate‐Promoted Synthesis of Enone Functionalized Benzo‐1,3‐Thiazines via Formal [4 + 2] Heteroannulation of Azadienes with β‐Ketodithioesters at Room Temperature

IF 4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2026-04-27 DOI:10.1002/adsc.70467

Ganesh Kumar, Nimisha Gupta, Keshav Raghuvanshi, Maya Shankar Singh

引用次数: 0

Abstract

An efficient approach for the direct synthesis of previously inaccessible enone functionalized benzo‐1,3‐thiazines has been developed via formal [4 + 2] heteroannulation of azadienes (generated in situ from 2‐aminobenzyl alcohol) with β‐ketodithioesters in acetonitrile at room temperature, facilitated by trimethylsilyl triflate (TMSOTf). This strategy is distinguished by transition‐metal and additive‐free mild conditions, convenient operation, wide functional group compatibility with no steric and electronic constraints, accessible scalability, high yields, and practical transformations. A combination of controlled experiments and HRMS studies corroborated the proposed mechanism.

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三甲基硅基三氟酸盐在室温下通过偶氮二烯与β -酮二硫酯的正[4 + 2]杂环反应促进烯酮功能化苯并1,3 -噻嗪的合成

在室温下，三甲基硅酸三酯（TMSOTf）催化氮偶氮烯（由2 -氨基苄醇原位生成）与β -酮二硫酯在乙腈中形成正[4 + 2]杂环反应，直接合成了以前难以获得的烯酮功能化苯- 1,3 -噻嗪。该策略的特点是不含过渡金属和添加剂，条件温和，操作方便，官能团兼容性广，没有空间和电子限制，可扩展性强，产率高，转化实用。对照实验和HRMS研究的结合证实了所提出的机制。

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.