Synthesis of Steroidal Thiadiazoles from Steroidal Ketones

M. Mushfiq, M. Alam, M. Akhtar
2005 Molecules  
Syntheses of steroidal heterocycles containing a five-membered N,Sheterocycle 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
more » ... mperature afforded the cyclized thiadiazole 4 and its 3β-acetoxy-and 3β-chloro analogues 5 and 6 in good yields.
doi:10.3390/10070803 pmid:18007350 fatcat:ibl2mxwd7va6hajbj7alxvy2mq