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Regioselective Synthesis of 2-Amino-Substituted 1,3,4-Oxadiazole and 1,3,4-Thiadiazole Derivatives via Reagent-Based Cyclization of Thiosemicarbazide Intermediate

Seung-Ju Yang, Seok-Hyeong Lee, Hyun-Jung Kwak and Young-Dae Gong*

*Center for Innovative Drug Library Research, Department of Chemistry, College of Science, Dongguk University, 26, 3-ga, Pil-dong Jung-gu, Seoul 100-715, Korea, Email: ydgongdongguk.edu

S.-J. Yang, S.-H. Lee, H.-J. Kwak, Y.-D. Gong, J. Org. Chem., 2013, 78, 438-444.

DOI: 10.1021/jo302324r (free Supporting Information)


Abstract

The reaction of a thiosemicarbazide intermediate with EDC·HCl in DMSO or p-TsCl, triethylamine in N-methyl-2-pyrrolidone gives the corresponding 2-amino-1,3,4-oxadiazoles and 2-amino-1,3,4-thiadiazoles through regioselcective cyclization processes.

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Key Words

1,3,4-Oxadiazoles, 1,3,4-Thiadiazoles


ID: J42-Y2013-0100