Synthesis of 2-Amino-1,3,4-oxadiazoles and 2-Amino-1,3,4-thiadiazoles via Sequential Condensation and I₂-Mediated Oxidative C-O/C-S Bond Formation

Pengfei Niu, Jinfeng Kang, Xianhai Tian, Lina Song, Hongxu Liu, Jie Wu, Wenquan Yu* and Junbiao Chang*

*College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, Henan 450001, China, Email: wenquan_yuzzu.edu.cn, changjunbiaozzu.edu.cn

P. Niu, J. Kang, X. Tian, L. Song, H. Liu, J. Wu, W. Yu, J. Chang, J. Org. Chem., 2015, 80, 1018-1024.

DOI: 10.1021/jo502518c

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Abstract

A transition-metal-free condensation of semicarbazide/thiosemicarbazide with aldehydes followed by I₂-mediated oxidative C-O/C-S bond formation provides 2-amino-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles in an efficient and scalable fashion.

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I₂-Mediated Oxidative C-O Bond Formation for the Synthesis of 1,3,4-Oxadiazoles from Aldehydes and Hydrazides

W. Yu, G. Huang, Y. Zhang, H. Liu, L. Dong, X. Yu, Y. Li, J. Chang, J. Org. Chem., 2013, 78, 10337-10343.

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Key Words

1,3,4-oxadiazoles, 1,3,4-thiadiazoles, iodine

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ID: J42-Y2015