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4-Alkylamino-2-chloroquinoline-3-carbonitriles 4a - c react with NaN 3  to give the corresponding tetrazolo[1,5-a]quinoline-4-carbonitriles 5a - c which are converted into 2-amino-quinoline-3-carbonitriles 8a - c by reaction with PPh 3  via an iminophosphorane and subsequent hydrolysis. On the other hand, the new 3,4-diamino-1H-pyrazolo[4,3-c]quinoline (11) was prepared by fusion of the aminoquinolines 8a - c with hydrazine hydrate. Diazotization of 11 followed by reaction with NaN 3  yielded the novel tetracyclic ring system 3-azido-1H-1,2,4,5,6,6a-hexaazabenzo[a]indacene (13)

Fused Quinoline Heterocycles IX: First Example of a 3,4-Diamino-1H-pyrazolo[4,3-c]quinoline and a 3-Azido-1H-1,2,4,5,6,6a-hexaazabenzo[a]indacene