76302-99-3Relevant articles and documents
Steroidal Heterocycles: Synthesis and Structure of Imidazothiazolo-, Thiazolobenzimidazolo-, and Thiazolo-s-triazolo-derivatives
Bajwa, Joginder S.,Sykes, Peter J.
, p. 2146 - 2151 (2007/10/02)
The condensation of 2α-bromo-5α-cholestan-3-one (1) with 2-mercaptoimidazole (2) in refluxing ethanol gave 5α-cholest-2-eno-(imidazothiazole) (5) and 3β-ethoxy-2'β,3'-dihydro-5α-cholestano-(imidazothiazole) (6), whereas the reaction of 2-mercaptoimidazole (2) with 16α-bromo-3-methoxyestra-1,3,5(10)-trien-17-one (7) gave the uncyclised product 16α-(imidazol-2-ylthio)-3-methoxyestra-1,3,5(10)-trien-17-one (8).Under analogous reaction conditions, the condensation of 2-mercaptoimidazole (2), 2-mercaptobenzimidazole (12), 3-mercapto-1,2,4-triazole (35), and their derivatives with 2α-bromo-3-oxo-steroids gave the expected cyclised products.However, from the condensation reactions between 3-mercapto-1,2,4-triazoles (35) and (36) with the 16α-bromo-17-oxo steroid (7) only 17β-ethoxy-3-methoxy-5',6'-dihydro-(thiazolo--s-triazole) (44) and its 2'-methyl derivative (45) were isolated.The structures of all the condensation products were determined with the help of i.r., 1H n.m.r., and 13C n.m.r. spectroscopy.
