Cascade Reaction of Isocyanides with Carboxylic Acid and CD3SSO3Na: Toward S-CD3 Thiocarbamates

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-29 DOI:10.1021/acs.orglett.5c01166

Xinyu Zhou, Kemeng Zhang, Shuodan Ding, Lijin Wang, Miaoying Li, Ke Wang, Jie Zhou, Ge Wu

引用次数: 0

Abstract

We developed an unprecedented cascade reaction involving isocyanides with carboxylic acids and CD₃SSO₃Na to access S-CD₃ thiocarbamates with the formation of two C–N bonds and one C–S bond. Preliminary mechanistic investigations disclose that these three-component reactions precede the esterification of carboxylic acids with isocyanides, generating a capable N-alkyl-N-formyl amide followed by thiolation with CD₃SSO₃Na to provide the corresponding products. The transformation has outstanding features in mild reaction conditions, effortless experimental operation, structural modification of polyfunctional carboxylic acid drugs, and large-scale preparation.

Abstract Image

查看原文本刊更多论文

异氰酸酯与羧酸和CD3SSO3Na级联反应制备S-CD3硫代氨基甲酸酯

我们开发了一个前所未有的级联反应，涉及异氰化物与羧酸和CD3SSO3Na，形成两个C-N键和一个C-S键，以获得S-CD3硫代氨基甲酸酯。初步的机理研究表明，这些三组分反应先于羧酸与异氰酸酯的酯化反应，生成n -烷基- n -甲酰基酰胺，然后与CD3SSO3Na进行硫代化，得到相应的产物。该转化具有反应条件温和、实验操作简便、多功能羧酸类药物结构修饰、制备规模大等突出特点。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

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.