Synthesis of nitrile derivatives of estrogens.
The first time synthesis of 7alpha- and 11beta-nitrile estradiol is described. Reaction of 7alpha-cyano-19-nortestosterone with copper(II)bromide in acetonitrile at room temperature results in aromatization of the A-ring. Treatment of 11beta-cyano-19-nortestosterone-17-one under similar condition does not induce A-ring aromatization but rather results in bromination at the 2beta-position. However A-ring aromatized products are obtained when the latter compound is treated with Ac2O-Py-AcOCl, NBS and HCl.
Ali
Hasrat
H
CIHR Group in the Radiation Sciences, Faculty of Medicine, Université de Sherbrooke, Sherbrooke, QC, Canada.
van Lier
Johan E
JE
D001965:Bromides; D003300:Copper; D004958:Estradiol / Q000737:chemistry; D045166:Estradiol Congeners / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008024:Ligands; D013058:Mass Spectrometry; D009277:Nandrolone / Q000031:analogs & derivatives* / Q000737:chemistry; D009570:Nitriles / Q000138:chemical synthesis*; D011960:Receptors, Estrogen / Q000187:drug effects
D001965:Bromides; D045166:Estradiol Congeners; D007202:Indicators and Reagents; D008024:Ligands; D009570:Nitriles; D011960:Receptors, Estrogen; D004958:Estradiol; C036443:17 alpha-cyanomethyl-19-nortestosterone; D009277:Nandrolone; D003300:Copper