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Synthesis 1997; 1997(7): 773-777
DOI: 10.1055/s-1997-1416
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Tetrazolo[1,5-a]quinolines and 1,2,3-Triazolo[1,5-a]quinazolines by the Action of Cyanocarbanions on 2-azidoarylcarbonyl Compounds

Thomas C. Porter, Robert K. Smalley* , Mabrouk Teguiche, Bambang Purwono
  • *Department of Chemistry and Applied Chemistry, University of Salford, Salford M5 4WT, UK, Fax +44(161)7455999
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Publication Date:
31 December 2000 (online)

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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 6a-f are formed. Triazoloquinazolines 9a-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-diphenylpropan-2-one.

tetrazolo[1,5-a]quinolines - 1,2,3-triazolo[1,5-a]quinazolines - 2-azidobenzaldehyde - 2-azidobenzonitrile - carbanions