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Molecules 2005, 10(7), 803-808; doi:10.3390/10070803
Article

Synthesis of Steroidal Thiadiazoles from Steroidal Ketones

* ,  and
Department of Chemistry, A.M.U., India
* Author to whom correspondence should be addressed.
Received: 2 August 2004 / Revised: 13 January 2005 / Accepted: 15 January 2005 / Published: 31 August 2005
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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.
Keywords: Thiadiazoles; steroidal thiadiazoles; steroidal heterocycles; cyclization; thionyl chloride; semicarbazide; dichloromethane. Thiadiazoles; steroidal thiadiazoles; steroidal heterocycles; cyclization; thionyl chloride; semicarbazide; dichloromethane.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Mushfiq, M.; Alam, M.; Akhtar, M. Synthesis of Steroidal Thiadiazoles from Steroidal Ketones. Molecules 2005, 10, 803-808.

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