Synthesis of Azasteroids with Pyrazoline and lsoxazoline Rings

Department of Chemistry, Nizam College, Hyderabad-500 001

Manuscript received 17 June 1992, accepted 21 September 1992

17-Oxo-5-androsten-3β-YI acetate (1) on reaction with dimethyl oxalate afforded the glyoxalate, 16-carbomethoxycarbonyl­17-oxo-5-androsten-3β-YI acetate (2) which on reaction with hydrazine hydrate, phenylhydrazine and hydroxyl amine hydro­chloride gave the corresponding 3β-acetoxy-5'-carbomethoxyandrost-5-en [17,16-c] pyrazole (3), 3β-acetoxy-5'-carbometh­oxy-1'-phenylandrost-5-en [17, 16-el pyrazole (4) and 3β-acetoxy-3'-carbomethoxyandrost-5-en [17, 16-c] isoxazole (5).