One-pot synthesis of N-arylated benzotriazoles and benzotriazinones via in situ diazotization and aryne trapping

Abstract

N-Arylated benzotriazoles and 1,2,3-benzotriazin-4-ones are important structural motifs in synthetic and medicinal chemistry, valued for their distinctive frameworks and functional versatility. We have developed an efficient, one-pot strategy for the synthesis of N-arylated benzotriazoles and benzotriazinones. The protocol involves in situ diazotization of o-phenylenediamine or 2-aminobenzamide using tert-butyl nitrite (^tBuONO), followed by trapping of arynes generated in situ from 2-(trimethylsilyl)aryltriflates in the presence of CsF. The methodology exhibits broad functional-group tolerance and was successfully applied to 47 substrates, affording yields in the range of 60–85%. Furthermore, gram-scale synthesis highlights the operational simplicity and practical utility of this approach.