Synthesis of Some Pyrazolo [Diazepine, Pyrazole, Isoxazole and Pyrimidine] Derivatives and Related Compounds

4-Arylidene-3-methyl-1-phenyl-2-pyrazolin-5-ones (1a-d) undergoes condensation with diethylmalonate, p-nitroacetophenone and/or 3-acetyl-pyridine under Michael condition to give compounds 2, 3 and 4, respectively. Treatment of 3 and 4 with hydrazine afforded the pyrazolodiazepines 7 and 8, respectively. Interaction of la with diethyl phenyl-malonate gave the Michael product 9, which undergoes hydrolysis, decarboxylation and cyclisation to give the indanone derivative (11). Condensation of 1c with hydrazine, hydroxylamine and urea gives compounds 12, 13 and 14, respectively. Cyclisation of the Michael compound 15 gives the benzopyranopyrazole (14). When 1c was subjected to Riemer-Tiemann reaction gives compounds 17 and 18. Acetic anhydride treatment of 18 gives the acetyl cresotic acid derivative (19).