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A combined experimental and theoretical study of the alkylation of 3,5‐dithioxo‐[1,2,4]triazepines
Author(s) -
Esseffar M.,
El Messaoudi M.,
Jalal R.,
Domingo L. R.,
Aurell M. J.
Publication year - 2008
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1348
Subject(s) - chemistry , alkylation , regioselectivity , benzene , medicinal chemistry , computational chemistry , organic chemistry , catalysis
The chemo‐ and regioselective alkylation reactions of 3,5‐dithioxo[1,2,4]triazepine 1 in a basic medium with α , ω ‐dibromoalkanes 2a – c , Br(CH 2 ) n Br ( n = 1–3), are studied experimentally and theoretically. These alkylations, which occur at the thioxo sulfur atom in position 5, afford mainly 5‐bromomethylthio‐2,7‐dimethyl‐ 2,3‐dihydro‐ 4H[1,2,4]triazepin‐3‐one 3 for n = 1, 6,8‐dimethyl‐5‐thioxo‐2,3,4,5‐tetrahydro‐6H[1,3]thiazolo[4,5‐d][1,2,4]triazepine 4 for n = 2 and 7,9‐dimethyl‐6‐thioxo‐2,3,4,5,6,7‐hexahydro[1,3]thiazino [4,5‐d][1,2,4]triazepine 5 for n = 3. Theoretical calculations have been carried out at the B3LYP/6‐31G* and B3LYP(benzene)/6‐311+G*//B3LYP/6‐31G* levels, in order to rationalize the experimental observations. Both chemo‐ and regio‐selectivities of the alkylation reactions are analyzed. Copyright © 2008 John Wiley & Sons, Ltd.