Friedländer condensation of 1H‐pyrazolin‐5‐ones with O‐aminobenzaldehydes. Synthesis of 1H‐pyrazolo[3,4‐B]quinolines

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Abstract
All the possible 1‐ and 3‐monomethyl, monophenyl, dimethyl, diphenyl, and methylphenyl‐1H‐pyrazolin‐5‐ones have been condensed with o‐aminobenzaldehyde. In some cases (but not all) 1‐H‐pyrazolo[3,4‐b]quinolines (10) are formed together with a variety of other products. The balance between formation of hydrazone 11 and the ring‐closed 10 is discussed, as is the formation of other products obtained in these condensations.