One-pot synthesis of N-substituted benzannulated triazoles via stable arene diazonium salts

McGrory, R., Faggyas, R. and Sutherland, A. (2021) One-pot synthesis of N-substituted benzannulated triazoles via stable arene diazonium salts. Organic and Biomolecular Chemistry, 19(27), pp. 6127-6140. (doi: 10.1039/D1OB00968K) (PMID:34179913)

Abstract

A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamides via stable diazonium salts, prepared using a polymer-supported nitrite reagent and p-tosic acid. The transformation was compatible with a wide range of aryl functional groups and amide/sulfonamide-substituents and was used for the synthesis of pharmaceutically important targets. The synthetic utility of the one-pot diazotisaton–cyclisation process was further demonstrated with the preparation of an α-amino acid containing 1,2,3-benzotriazin-4(3H)-one.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Sutherland, Professor Andrew and McGrory, Rochelle and Faggyas, Réka
• Authors: McGrory, R., Faggyas, R., and Sutherland, A.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Organic and Biomolecular Chemistry
• Publisher: Royal Society of Chemistry
• ISSN: 1477-0520
• ISSN (Online): 1477-0539
• Published Online: 22 June 2021
• Copyright Holders: Copyright © The Royal Society of Chemistry 2021
• First Published: First published in Organic and Biomolecular Chemistry 19(27): 6127-6140
• Publisher Policy: Reproduced under a Creative Commons licence