Access to benzo[e][1,3]thiazin-4-ones via PCy3-mediated annulations of benzo[c][1,2]dithiol-3-ones with iso(thio)cyanates

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-08-05 DOI:10.1039/d5qo01013f

Chengxiang Yi, Mingyang Zhu, Jie Ren, Weimin Zhu, Chuanjun Song, Yangang Wu

引用次数: 0

Abstract

Herein, we describe a novel organophosphine-mediated annulation reaction of benzo[c][1,2]dithiol-3-ones with iso(thio)cyanates, which proceeds via an S atom to C-N unit exchange strategy. The methodology efficiently produced a variety of benzo[c][1,2]dithiol-3-one derivatives in moderate to excellent yields under straightforward reaction conditions. Other salient features of this approach include the transition-metal-free, operational simplicity, gram-scale synthesis, and capacity for late-stage modifications. Additionally, control experiments were conducted to provide new insights into the conversion mechanism of benzo[c][1,2]dithiol-3-ones.

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pcy3介导苯并[c][1,2]二硫醇-3-酮与异（硫）氰酸酯环的合成[e][1,3]噻嗪-4-酮

在此，我们描述了一种新的有机膦介导的苯并[c][1,2]二硫醇-3- 1与异（硫）氰酸酯的环化反应，该反应通过S原子到c - n单元交换策略进行。该方法在简单的反应条件下，以中等至优异的收率高效地制备了多种苯并[c][1,2]二硫醇-3- 1衍生物。这种方法的其他显著特点包括无过渡金属、操作简单、克级合成以及后期修改的能力。此外，通过对照实验对苯并[c][1,2]二硫醇-3-酮的转化机理有了新的认识。

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 Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.