A Facile Synthesis of 2-Aminobenzoxazoles and 2-Aminobenzimidazoles Using N-Cyano-N-phenyl-p-toluenesulfonamide (NCTS) as an Efficient Electrophilic Cyanating Agent

Mahesh Kasthuri*, H. Sharath Babu, K. Shiva Kumar, Ch. Sudhakar, P. V. Nagendra Kumar

*Department of Chemistry, GITAM University, Hyderabad Campus, Rudraram Village, Patancheru Mandal, Medak Dist., Telangana State, 502 329, India, Email: mahesh.kasthurigitam.in

M. Kasthuri, H. S. Babu, K. S. Kumar, Ch. Sudhakar, P. V. N. Kumar, Synlett, 2015, 26, 897-900.

DOI: 10.1055/s-0034-1380166

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Abstract

The reaction of N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) as nonhazardous electrophilic cyanating agent with various substituted 2-aminophenols and benzene-1,2-diamine enables a facile synthesis of 2-aminobenzoxazole and 2-aminobenz­imidazole derivatives in the presence of lithium hexamethyldisilazide (LiHMDS). This protocol offers operational simplicity, short reaction time, and simple workup.

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Key Words

benzoxazoles, benzimidazoles, electrophilic cyanation

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ID: J60-Y2015