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The reaction of the 2-arylhydrazonopropanal 3a with 2-amino1,1,3-tricyanopropene 4 afforded the pyridopyridazines 6. On the other hand, reaction of 3b with 4 afforded 7. Compounds 3a,b also condensed with 2-aminobenzimidazole and 3(5)-amino-1,2,4-triazole to yield azolopyrimidines 10 and 13. Refluxing compounds 3a,b in acetic acid in the presence of ammonium acetate afforded 2,3,6,7-tetraaza-bicyclo[3.3.1]nona-3,7-diene 14 and aroylcinnoline 15 respectively.

zeitschrift für naturforschung b

Pyridopyridazines, Benzimidazolopyrimidines Triazolopyrimidines, 9-Oxo-2,3,6,7-tetraazabicyclo[3.3.1]nona-3,7-diene and Aroylcinnolines from 2-Arylhydrazono-3-oxopropanals