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

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 thioamid...

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Bibliographic Details
Published in:MolBank 2001-05, Vol.6 (6), p.557-573
Main Authors: Fathalla, Walid, Cajan, Michal, Pazdera, Pavel
Format: Article
Language:English
Subjects:
3-a]quinazolin-5-one
4-methyl-1-thioxo- 1
4]triazolo
5-tetrahydro
Cyclic thioamides
DFT computational studies
Nitrogen
regioselective reactions
Sulfur
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Summary: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.
ISSN:1420-3049
1420-3049
1422-8599
DOI:10.3390/60600557