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79. Synthesis of 4-Azido-3-diazo-3H-pyrazolo[3,4-b]quinoline from 3-Amino-4-hydrazino-1H-pyrazolo[3,4-b]quinoline. (Organic azides in heterocyclic synthesis, part 28).
Wolfgang Stadlbauer and Gerhard Hojas, J. Chem. Soc., Perkin Trans. 1, 3085-3087 (2000).

Abstract:

The reaction of 3-amino-4-hydrazino-1H-pyrazolo[3,4-b]quinoline 8 with nitrous acid did not give 2,4-diazidoquinoline-3-carbonitrile 5 as reported previously, but afforded in 60% yield 4-azido-3-diazo-pyrazolo[3,4-b]quinoline 10, which gave by azo coupling 4-azido-3-(2-hydroxy-1-naphthyl)-1H-pyrazolo[3,4b]quinoline 11.


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