Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/24699
Title: On the mechanism and stereochemistry of the formation of beta-lactam derivatives of 2,4-disubstituted-2,3-dihydro-benzo[1,4]diazepines
Authors: Wang, HZ
Zhou, X
Xu, JX
Jin, S
Li, YM
Chan, ASC
Issue Date: 2001
Publisher: Hetero Corporation
Source: Journal of heterocyclic chemistry, 2001, v. 38, no. 5, p. 1031-1034 How to cite?
Journal: Journal of Heterocyclic Chemistry 
Abstract: 2-Chloro-4-phenyl-2a-(4'-methoxyphenyl)-3,5-dihydroazatetracyclic[1,2-d]benzo[1,4]diazepin-1-one (IIIa) and 2-chloro-4-methyl-2a-(4'-methoxyphenyl)-3,5-dihydroazatetracyclic[1,2-d]-benzo[1,4]diazepin-1-one (IIIb) were synthesized. 1-Benzoyl-2-phenyl-4-(4'-methoxyphenyl)[1,4]-benzodiazepine (IIa) was formed through benzoylation of starting material 2-phenyl-4-(4'-methoxyphenyl)-[1,4]benzodiazepine (I-a) with the inversion of seven-member ring boat conformation. The thus formed beta -lactams should have four pairs of stereoisomers. However, only one pair of enantiomers (2S,2aR,4R) and (2R,2aS,4S) was obtained. The mechanism and stereochemistry of the formation of these compounds were studied on the basis of nmr spectroscopy and further confirmed by X-ray diffraction.
URI: http://hdl.handle.net/10397/24699
ISSN: 0022-152X
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