On the mechanism and stereochemistry of the formation of beta-lactam derivatives of 2,4-disubstituted-2,3-dihydro-benzo[1,4]diazepines

Citation
Hz. Wang et al., On the mechanism and stereochemistry of the formation of beta-lactam derivatives of 2,4-disubstituted-2,3-dihydro-benzo[1,4]diazepines, J HETERO CH, 38(5), 2001, pp. 1031-1034
Citations number
11
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022-152X → ACNP
Volume
38
Issue
5
Year of publication
2001
Pages
1031 - 1034
Database
ISI
SICI code
0022-152X(200109/10)38:5<1031:OTMASO>2.0.ZU;2-Q
Abstract
2-Chloro-4-phenyl-2a-(4'-methoxyphenyl)-3,5-dihydroazatetracyclic[1,2-d]ben zo[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 synthes ized. 1-Benzoyl-2-phenyl-4-(4'-methoxyphenyl)[1,4]-benzodiazepine (IIa) was formed through benzoylation of starting material 2-phenyl-4-(4'-methoxyphe nyl)-[1,4]benzodiazepine (I-a) with the inversion of seven-member ring boat conformation. The thus formed beta -lactams should have four pairs of ster eoisomers. 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 confir med by X-ray diffraction.