The Preparation and Crystal structure of 16-Acetylandrosta-4,16-Dien-3-One⁺

Abstract

Dehydroisoandrosterone was formylated at C-16 by a Vilsmeier reaction and by condensation with methyl formate. The product of the latter reaction was converted to 16-acetylandrosta-4,16-dien-3-one and its X-ray crystal structure was determined.

N‐alkyl‐4‐chloro‐1H‐benzo[c][1,2]thiazine‐3‐carbaldehyde‐2,2‐dioxides—New functional benzothiazine derivatives

“…During the last 25 years, chloroformylation became a convenient transformation providing access to the intermediates widely used in pharmaceutical-directed organic synthesis [6][7][8][9][10]. The novel -chloroaldehyde compounds 5 contain two electrophilic centers: the carbon atom C-4 of the benzothiazine system and the carbon atom of the aldehyde group.…”

“…Product 7e (68%): H NMR (400 MHz, DMSO): = 5.21 (s, 2H), 6.82 (t, J = 6.8 Hz, 2H), 7.12-7.35 (m, 11H), 7.44 (t, J = 7.8 Hz, 1H), 7.89 (d, J = 7.6 Hz, 1H) 8.0 (s, 1H), 11.0 (s, 1H); 13 C NMR (100 MHz, DMSO): = 51. 6,113.6,120.6,121.3,123.3,125.3,127.5,127.7,127.9,128.4,128.5,129.0,129.3,130.0,131.1,132.1,133.1,136.7,137.8,144.6;Anal. calcd.…”

Steroids: reactions and partial synthesis

“…The preparation and X-ray crystal structure of 16-acetylandrosta-4,16-diene-3-one 17 has been reported. 61 The conditions for the abnormal Beckmann rearrangement of steroidal C-17 oximes have been optimized 62 for the fragmentation of ring D to form 18. 16,17-Secosteroids with aminomethylene-2-pyridine structures have been used 63 as chiral ligands for the copper ion activation of oxygen.…”