Heterocyclisch anellierte Steroide aus 2‐Hydroxymethylen‐canrenon

Abstract

A-ring annulated heterocycles, the isoxazole 6, the pyrazoles 8 and the pyrimidines 9 are prepared starting from 2-hydroxymethylene canrenone 1. Binding studies were carried out with the compounds 1 and 6-8 using estrogen, progesterone, androgen, gluco- and mineralocorticoid receptors as well as the serum proteins SHBG and CBG: the substances were inactive on the receptor level. 1, 7 and 8a show weak binding affinity to CBG.

Molecular Construction Using Formamide as a C1 Feedstock

“…used another butenone in formamide and ammonium chloride to produce 4‐trifluoromethyl pyrimidine in 23 % yield (1 h, 160–180 °C). In 1995, Gorlitzer et al [16g] . used hydroxy butanone by refluxing in formamide for 2 h under a N 2 atmosphere, and pyrimidine was obtained with 53 % yield.…”