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1H-4,5,6,7-Tetrahydro-1,3-diazepines. part II: basicity and hydrolysis of 1, 2-diaryl derivatives

✍ Scribed by Mónica E. Hedrera; Isabel A. Perillo; Beatriz Fernández

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
83 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Basicity and alkaline hydrolysis of 1,2‐diaryl‐1__H__‐4,5,6,7‐tetrahydro‐1,3‐diazepines 1 are studied. Results are analyzed on the basis of Hammett and Swain‐Lupton constants, finding good structure‐basicity correlation when both, inductive and mesomeric effects, are considered together. Regioselectivity 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: 1__H__‐4, 5‐dihydroimidazoles and 1,4,5,6‐tetrahydropyirimidines respectively.

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