ONE-STEP CONVERSION OF OXETANE-FUSED TO 1,3-OXAZINE-FUSED STEROIDS

Authors
HAJNAL A WOLFLING J SCHNEIDER G
Citation
A. Hajnal et al., ONE-STEP CONVERSION OF OXETANE-FUSED TO 1,3-OXAZINE-FUSED STEROIDS, Collection of Czechoslovak Chemical Communications, 63(10), 1998, pp. 1613-1622
Citations number
22
Categorie Soggetti
Chemistry
Journal title
Collection of Czechoslovak Chemical Communications → ACNP
ISSN journal
00100765
Volume
63
Issue
10
Year of publication
1998
Pages
1613 - 1622
Database
ISI
SICI code
0010-0765(1998)63:10<1613:OCOOT1>2.0.ZU;2-5
Abstract
In a ring-expansion reaction, alkyl and aryl nitriles, in the presence of tetrafluoroboric acid-diethyl ether complex, react with 3-methoxy- 16 beta, 17 beta-dihydro-4'H-oxeto[3',2': 16,17]estra-1,3,5(10)-triene to give 3-methoxy-16 beta,17 beta-dihydro-4'H-[1,3]-oxazino[5',6':16, 17]estra-1,3,5(10)-triene derivatives. Under similar conditions 3-met hoxy-16 alpha, 17 alpha-dihydro-4'H-oxeto[3',2': 16,17]estra-1,3,5(10) -triene undergoes a Wagner-Meerwein rearrangement.