Electrophile-induced generation of cyclic azomethine imines from steroidal delta-alkenyl hydrazones.
Novel delta-alkenyl phenylhydrazones were synthesized in both the estrone and the 13alpha-estrone series. Electrophile-induced cyclizations of alkenyl phenylhydrazones with phenylselenyl bromide furnished cyclic iminium salts, via attack of the imino nitrogen atom on the intermediate seleniranium ion. Hydride reduction of the iminium salts led to novel aminophenyl-substituted aza-D-homoestrones. The structures of the new products were determined by NMR (one- and two-dimensional) and MALDI-MS techniques, with C(70) fullerenes as matrix in the latter case.
Mernyák
Erzsébet
E
Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary. bobe@chem.u-szeged.hu
Márk
László
L
Frank
Eva
E
Schneider
Gyula
G
Wölfling
János
J
D001391:Azo Compounds / Q000737:chemistry*; D003500:Cyclization; D006835:Hydrazones / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013256:Steroids / Q000737:chemistry*; D013882:Thiosemicarbazones / Q000737:chemistry*
D001391:Azo Compounds; D006835:Hydrazones; D007097:Imines; D007202:Indicators and Reagents; D013256:Steroids; D013882:Thiosemicarbazones; C512188:azomethine