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Title: Synthesis of substituted steroidal thiadiazole, triazole and oxidotriazole
Authors: Shamsuzzaman
Siddiqui, Tabassum
Alam, Mohd. Gulfam
Keywords: Steroidal thiadiazole;Triazole;Oxidotriazole;Ethyl chloroacetate;Heterocyclization
Issue Date: Dec-2007
Publisher: CSIR
Abstract: Ethyl-5-cholesten-3β-O-acetate 2 and its thiosemicarbazide 3 have been synthesized by the reaction of 3β-hydroxycholest-5-ene 1 with ethyl chloroacetate and 2 with thiosemicarbazide in 1,4 dioxane, respectively. The thiosemicarbazide 3 on chemoselective heterocyclization with conc. H₂SO₄, conc. NaOH and iodine in the presence of alkali separately afforded 3β-[5'-amino-1',2',4'-thiadiazole-3'-methoxy]-cholest-5-ene 4,3β-[5'-mercapto-1',2',4'-triazole-3'-methoxy]-cholest-5-ene 5 and 3β-[5'-mercapto-3',5'-oxido-1',2',4'-triazolo-3'-methoxy]-5⍺-cholestane 6, respectively. The structures of these compounds have been established on the basis of elemental, analytical and spectral data.
Page(s): 2068-2070
Appears in Collections:IJC-B Vol.46B(12) December 2007]

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