Synthesis of Steroidal Thiadiazoles from Steroidal Ketones

Author： Mushfiq M.   Alam Mahboob   Akhtar Mohd. Shaheer  

Publisher： MDPI

E-ISSN： 1420-3049|10|7|803-808

ISSN： 1420-3049

Source： Molecules, Vol.10, Iss.7, 2005-08, pp. : 803-808

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Abstract

Syntheses of steroidal heterocycles containing a five-membered N,S- heterocycle attached at the 6,7 positions of the B ring are reported. 5α-Cholestane-6-one (1), its 3β-acetoxy- (2) and 3β-chloro- (3) analogues reacted with semicarbazide and aqueous sodium acetate in refluxing ethanol to yield 5α-cholestan-6-one-semicarbazone 1a and its 3-β-acetoxy and 3β-chloro derivatives 2a and 3a, respectively. The reactions of 1a, 2a and 3a with thionyl chloride in dichloromethane at low temperature afforded the cyclized thiadiazole 4 and its 3β-acetoxy- and 3β-chloro analogues 5 and 6 in good yields.

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