Issue 0, 1980

Steroidal heterocycles: synthesis and structure of imidazo[2,1-b]thiazolo-, thiazolo[3,2-a]benzimidazolo-, and thiazolo[3,2-b]-s-triazolo-derivatives

Abstract

The condensation of 2α-bromo-5α-cholestan-3-one (1) with 2-mercaptoimidazole (2) in refluxing ethanol gave 5α-cholest-2-eno[2,3-b]-(imidazo[2,1-b]thiazole)(5) and 3β-ethoxy-2′β,3′-dihydro-5α-cholestano[2,3-b](imidazo[2,1-b]thiazole)(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 [16,17-e]-(thiazolo-[3,2-b]-(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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1980, 2146-2151

Steroidal heterocycles: synthesis and structure of imidazo[2,1-b]thiazolo-, thiazolo[3,2-a]benzimidazolo-, and thiazolo[3,2-b]-s-triazolo-derivatives

J. S. Bajwa and P. J. Sykes, J. Chem. Soc., Perkin Trans. 1, 1980, 2146 DOI: 10.1039/P19800002146

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