regioselectivity of electrophilic attack on 4-methyl-1-thioxo-1,2,4,5-tetrahydro[1,2,4]triazolo[4,3-a]quinazolin-5-one. part 1: reactions at the sulfur atom
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ID: 234812
2001
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Abstract
The regioselectivity of the model compound 4-methyl-1-thioxo-1,2,4,5-tetrahydro[1,2,4]triazolo[4,3-a]quinazolin-5-one (3) towards different electrophiles was studied. Compound 3 reacts with alkyl and aryl halides to give the corresponding S-substituted derivatives. The reaction of the model thioamide with acyl halides proceeds by the formation of kinetically controlled S-acyl derivatives followed by a transacylation reaction to give the N2-acyl derivatives as thermodynamically controlled products. Theoretical DFT computational studies supported the explanation of these results. The synthesized compounds were characterized by FTIR, 1H-NMR, 13C-NMR, and mass spectroscopy.
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pazdera2001moleculesregioselectivity
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| Authors | ;Pavel Pazdera;Michal Čajan;Walid Fathalla |
| Journal | Journal of ethnopharmacology |
| Year | 2001 |
| DOI |
10.3390/60600557
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| URL | |
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