Tetrazolo[1,5-a]quinolines and 1,2,3-triazolo[1,5-a]quinazolines by the action of cyanocarbanions on 2-azidoarylcarbonyl compounds

摘要

In protic solvents, 2-azidobenzaldehyde undergoes base-catalysed condensation with cyanocarbanions to yield tetrazolo[1,5-a]quinolines 5a-g, whereas in aprotic media 1,2,3-triazolo[1,5-a]quinazolines 6 a-f are formed. Triazoloquinazolines 9 a-g are also obtained from 2'-azidoacetophenone and from 2-azidobenzonitrile, whereas with 2-azidobenzoyl chloride hydroxytetrazoloquinolines 13a,b result. 2,1-Oxazolo[4,3-c]tetrazolo[1,5-a]quinolines 20a,b are obtained by the action of selected cyanocarbanions on 2-azidobenzonitrile oxide 15 and a 1,2,3-triazolo[1,5-a]quinoline 22 by base-catalysed condensation of 2-azidobenzonitrile with 1,3-diphenyl propan-2-one.