M. Gibson, M. Green
1965
Citations
0
Influential Citations
14
Citations
Journal
Tetrahedron
Abstract
Abstract 3-Amino-1,2,3-benzotriazin-4-one hydrolysed in alkaline solution decomposes by two mechanisms: (i) by prototropic shift and loss of nitrogen to give o-hydrazinobenzoic acid, and (ii) by loss of amide ion (ammonia) to give o-azidobenzoic acid. Course (i) can be diminished in importance or excluded by appropriate modification of the 3-amino group. In hot aqueous hydrochloric acid, 3-acetamido-1,2,3-benzotriazin-4-one undergoes ring fission, trans-nitrosation and loss of acetic acid to give anthranilazide, which then rearranges to benzimidazolone with loss of nitrogen.