Synthesis and stereochemistry of 8,13-diaza-2,3-dimethoxygona-1,3,5(10),9(11)-tetraen-12-one and D-homo derivatives.
From the condensation reaction of O-methylbutyrolactim (2), O-methylvalerolactim (3), O-methylcaprolactim (4) and O-methyl-4-t-butylcaprolactim (5) with ethyl 6,7-dimethoxy-alpha-[1-(1,2,3,4-tetrahydro-isoquinolyl)] acetate (1), 8,13-diaza-2,3-dimethoxygona-1,3,5(10),9(11)-tetraen-1 2-one (6) D-homo-derivatives (7-9), and medium-sized ring cyclic diamides (10,11) were obtained. The stereoselective reduction of compounds 6-9 by Adam's platinum catalyst afforded 8,13-diaza-2,3-dimethoxygona-1,3,5(10)-trien-12-one (12) and its D-homo derivatives (13-15). The structures of the compounds obtained were established by NMR and X-ray crystallographic analyses.
Göndös
G
G
Department of Organic Chemistry, József Attila University, Szeged, Hungary.
Gera
L
L
Tóth
G
G
Kálmán
A
A
Bridson
J
J
D001378:Azasteroids / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D014961:X-Ray Diffraction
C114267:8,13-diaza-2,3-dimethoxygona-1,3,5(10),9(11)-tetraen-12-one; D001378:Azasteroids