Atropisomeric properties of the dibenzo[b,d]azepin-6-one nucleus.
Dibenzo[b,d]azepin-6-ones (2a,b) were separated by chiral HPLC into the aR- and aS-atropisomers with high stereochemical stability, and methylation at C7 of 2a stereoselectively gave the (aR*,7R*) isomer (4a), which converted to the thermodynamically stable (aS*,7R*) atropisomer (5a) after heating.
School of Pharmaceutical Sciences, Teikyo University, 1091-1 Sagamiko, Sagamihara, Kanagawa 229-0195, Japan.
Hidetsugu
H
Tabata
Kumi
K
Akiba
Shoukou
S
Lee
Hideyo
H
Takahashi
Hideaki
H
Natsugari
D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D001554:Benzene / Q000737:chemistry*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D001381:Azepines; D001554:Benzene