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Communication | Special issue | Vol 101, No. 2, 2020, pp.444-451
Published online, 1st October, 2019
DOI: 10.3987/COM-19-S(F)46
Synthesis of 2-Amino-1,3-benzoselenazole via Metal-Free Cyclization from Isothiocyanate and Bis(o-aminophenyl)diselenide

Hayato Ichikawa,* Naoka Miyashi, Yui Ishigaki, and Minako Mitsuhashi

*Department of Applied Molecular Chemistry, College of Industrial Technology, Nihon University, 1-2-1, Izumi-cho, Narashino, Chiba 275-8575, Japan

Abstract

Amino-1,3-benzoselenazoles were generated from the reactions of bis(o-aminophenyl)diselenide and various isothiocyanates under metal-free cyclization conditions. The cyclization of isothiocyanate bearing bulky substituents proceeded in excellent yields because the amounts of byproducts generated were reduced. Acid hydrolysis of acetamide produced 2-amino-1,3-benzoselenazole (4).