Synthesis 2023; 55(13): 2091-2098
DOI: 10.1055/a-2035-2873
paper
Special Issue Honoring Prof. Guoqiang Lin's Contributions to Organic Chemistry

Visible-Light-Promoted C(sp3)–H Bond Functionalization toward Aminothiazole Skeletons from Active Methylene Ketones and Thioureas

Renhua Zheng 
a   School of Pharmaceutical and Chemical Engineering, Taizhou University, Shifu Avenue 1139, Jiaojiang, 318000, P. R. of China
,
Xiurong Hu
a   School of Pharmaceutical and Chemical Engineering, Taizhou University, Shifu Avenue 1139, Jiaojiang, 318000, P. R. of China
b   Department of Chemistry, Zhejiang Sci-Tech University, 2 Street 928, Hangzhou, 310018, P. R. of China
,
Huajiang Jiang
a   School of Pharmaceutical and Chemical Engineering, Taizhou University, Shifu Avenue 1139, Jiaojiang, 318000, P. R. of China
,
Haichang Guo∗
a   School of Pharmaceutical and Chemical Engineering, Taizhou University, Shifu Avenue 1139, Jiaojiang, 318000, P. R. of China
,
Lei Wang  ∗
a   School of Pharmaceutical and Chemical Engineering, Taizhou University, Shifu Avenue 1139, Jiaojiang, 318000, P. R. of China
c   Advanced Research Institute and School of Pharmaceutical Sciences, Taizhou University, Shifu Avenue 1139, Jiaojiang, 318000, P. R. of China
› Author AffiliationsWe gratefully acknowledge the Natural Science Foundation of Zhejiang Province (LZ22B020003) and the National Natural Science Foundation of China (22071171) for financial support of this work.
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This paper is dedicated to Professor Guoqiang Lin on the occasion of his 80th birthday.

Abstract

A novel and efficient visible-light-induced method is developed for the one-pot synthesis of functionalized 2-aminothiazoles from easily accessible active methylene ketone derivatives and different thioureas at room temperature. The mild reaction conditions, green chemistry, straightforward work-up, and high yields of the products make this procedure useful for the construction of 2-aminothiazole derivatives.

Key words

photocatalysis - 2-aminothiazoles - cyclization - free-radical reaction - heterocyclic compounds

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2035-2873.
  • Supporting Information


Publication History

Received: 23 December 2022

Accepted after revision: 14 February 2023

Accepted Manuscript online:
14 February 2023

Article published online:
13 March 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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