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无金属条件下通过三组分氧化环化反应构建 2-芳基苯并噻唑。

Assembly of 2-Arylbenzothiazoles through Three-Component Oxidative Annulation under Transition-Metal-Free Conditions.

机构信息

Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University , Xiangtan 411105, China.

Beijing National Laboratory for Molecular Sciences and CAS Key Laboratory of Molecular Recognition and Function Institute of Chemistry, Chinese Academy of Sciences (CAS) , Beijing 100190, China.

出版信息

Org Lett. 2017 Sep 1;19(17):4576-4579. doi: 10.1021/acs.orglett.7b02168. Epub 2017 Aug 17.

DOI:10.1021/acs.orglett.7b02168
PMID:28817291
Abstract

Highly efficient methods for the synthesis of 2-arylbenzothiazoles and 2-arylnaphtho[2,1-d]thiazoles have been developed. Readily available aromatic amines, benzaldehydes, and elemental sulfur were directly assembled through oxidative annulation and C-H functionalization under transition-metal-free conditions, where DMSO or oxygen served as the oxidant. NHI or KI as the catalyst was found to be effective to promote the transformations to give the annulation products in good to excellent yields with wide functional group tolerance.

摘要

开发了高效的合成 2-芳基苯并噻唑和 2-芳基萘并[2,1-d]噻唑的方法。在无过渡金属条件下,通过氧化环化和 C-H 功能化,可直接将易得的芳基胺、苯甲醛和元素硫组装在一起,其中 DMSO 或氧气用作氧化剂。发现 NHI 或 KI 作为催化剂可有效地促进转化,以良好至优异的收率获得具有广泛官能团耐受性的环化产物。

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