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@article{362912,
author = {Mohamed, Walid Fathalla and Čajan, Michal and Pazdera, Pavel},
article_location = {Basel},
article_number = {5},
keywords = {Cyclic thioamides; regioselective reactions; 4-methyl-1-thioxo-1;2;4;5-tetrahydro[1;2;4]triazolo[4;3-a]quinazolin-5-one; DFT computational studies.},
language = {eng},
issn = {1420-3049},
journal = {Molecules},
title = {Regioselectivity of Electrophilic Attack on 4-Methyl-1-thioxo-1,2,4,5-tetrahydro[1,2,4]triazolo[4,3-a]quinazolin-5-one.},
volume = {6},
year = {2001}
}
TY - JOUR
ID - 362912
AU - Mohamed, Walid Fathalla - Čajan, Michal - Pazdera, Pavel
PY - 2001
TI - Regioselectivity of Electrophilic Attack on 4-Methyl-1-thioxo-1,2,4,5-tetrahydro[1,2,4]triazolo[4,3-a]quinazolin-5-one.
JF - Molecules
VL - 6
IS - 5
SP - 557
EP - 557
PB - MDPI
SN - 14203049
KW - Cyclic thioamides
KW - regioselective reactions
KW - 4-methyl-1-thioxo-1;2;4;5-tetrahydro[1;2;4]triazolo[4;3-a]quinazolin-5-one
KW - DFT computational studies.
N2 - 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.
ER -
MOHAMED, Walid Fathalla, Michal ČAJAN and Pavel PAZDERA. Regioselectivity of Electrophilic Attack on 4-Methyl-1-thioxo-1,2,4,5-tetrahydro[1,2,4]triazolo[4,3-a]quinazolin-5-one. \textit{Molecules}. Basel: MDPI, 2001, vol.~6, No~5, p.~557-573. ISSN~1420-3049.
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