Chemodivergent Photocatalyzed Heterocyclization of Hydrazones and Isothiocyanates for the Selectivity Synthesis of 2-Amino-1,3,4-thiadiazoles and 1,2,4-Triazole-3-thiones

Qing-Hu Teng; Feng-Lai Lu; Kai Wang; Li-Ya Zhou; Dian-Peng Li

doi:10.1021/acs.joc.3c00320

Chemodivergent Photocatalyzed Heterocyclization of Hydrazones and Isothiocyanates for the Selectivity Synthesis of 2-Amino-1,3,4-thiadiazoles and 1,2,4-Triazole-3-thiones

J Org Chem. 2023 Jun 2;88(11):7104-7116. doi: 10.1021/acs.joc.3c00320. Epub 2023 May 4.

Authors

Qing-Hu Teng^{1

2

3}, Feng-Lai Lu¹, Kai Wang³, Li-Ya Zhou², Dian-Peng Li^{1

2}

Affiliations

¹ Guangxi Key Laboratory of Plant Functional Phytochemicals and Sustainable Utilization, Guangxi Institute of Botany, Guangxi Zhuang Autonomous Region and Chinese Academy of Sciences, Guilin 541006, P. R. China.
² School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, People's Republic of China.
³ Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional Materials, College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, China.

PMID: 37141629
DOI: 10.1021/acs.joc.3c00320

Abstract

A photocatalytic chemodivergent reaction for the selectivity formation of C-S and C-N bonds in a controlled manner was proposed. The reaction medium, either neutral or acidic, is critical to dictate the formation of 2-amino-1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones from isothiocyanates and hydrazones. This is a practical protocol to achieve the chemoselectivity under mild and metal-free conditions.