Synthesis of pregnene and androstane heterocyclic derivatives of potential pharmacological activity

The synthesis of steroidal heterocycles containing the pyrazole, pyrimidine and isoxazole ring attached to pregnene nucleus is reported Progesterone [1] reacted with methoxyphenylthiosemicarbazide [2] to afford the thiosemicarbazoncprogesterone 3, which reacted with either malononitile or ethyl cyanoacetate to afford the condensed products 5a,b. The scope and limitation of compounds 5a,b were studied to form hetemcyclic ring systems. Also, the aminothiophenylandrostene derivatives 14a,b were synthesized and the reactivity of the amino group towards the formation of the biologically active sultam rings was studied.