1H-4,5,6,7-tetrahydro-1,3-diazepines. Part II: Basicity and hydrolysis of 1,2-diaryl derivatives

Citation
Me. Hedrera et al., 1H-4,5,6,7-tetrahydro-1,3-diazepines. Part II: Basicity and hydrolysis of 1,2-diaryl derivatives, J HETERO CH, 38(4), 2001, pp. 895-900
Citations number
29
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022152X → ACNP
Volume
38
Issue
4
Year of publication
2001
Pages
895 - 900
Database
ISI
SICI code
0022-152X(200107/08)38:4<895:1PIBAH>2.0.ZU;2-Q
Abstract
Basicity and alkaline hydrolysis of 1,2-diaryl-1H-4,5,6,7-tetrahydro-1,3-di azepines 1 are studied. Results are analyzed on the basis of Hammett and Sw ain-Lupton constants, finding good structure-basicity correlation when both , inductive and mesomeric effects, are considered together. Regioselectivit y is observed in the alkaline hydrolysis of compounds 1, and it is analyzed in light of the stereoelectronic control theory. Results are compared with those previously obtained for five and six membered ring homologues: 1H-4, 5-dihydroimidazoles and 1,4,5,6-tetrahydropyirimidines respectively.