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RESEARCH PRODUCT
A combined experimental and theoretical study of the alkylation of 3,5-dithioxo-[1,2,4]triazepines
Rachid JalalMaría José AurellM. EsseffarLuis R. DomingoM. El Messaoudisubject
chemistry.chemical_compoundchemistryStereochemistryOrganic ChemistrySN2 reactionRegioselectivityPhysical and Theoretical ChemistryAlkylationBenzenedescription
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(CH2)nBr (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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2008-01-01 | Journal of Physical Organic Chemistry |