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. Molecules. Basel: MDPI, 2001, vol. 6, No 5, p. 557-573. ISSN 1420-3049.
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Basic information
Original name Regioselectivity of Electrophilic Attack on 4-Methyl-1-thioxo-1,2,4,5-tetrahydro[1,2,4]triazolo[4,3-a]quinazolin-5-one.
Authors MOHAMED, Walid Fathalla, Michal ČAJAN and Pavel PAZDERA.
Edition Molecules, Basel, MDPI, 2001, 1420-3049.
Other information
Original language English
Type of outcome Article in a journal
Field of Study 10401 Organic chemistry
Country of publisher Switzerland
Confidentiality degree is not subject to a state or trade secret
Impact factor Impact factor: 0.223
RIV identification code RIV/00216224:14310/01:00004227
Organization unit Faculty of Science
Keywords in English 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.
Tags 2, 3-a]quinazolin-5-one, 4, 4-methyl-1-thioxo-1, 4]triazolo[4, 5-tetrahydro[1, Cyclic thioamides, DFT computational studies., regioselective reactions
Changed by Changed by: doc. RNDr. Pavel Pazdera, CSc., učo 2276. Changed: 6/6/2001 11:54.
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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MSM 143100011, plan (intention)Name: Struktura a vazebné poměry, vlastnosti a analýza syntetických a přírodních molekulových ansamblů
Investor: Ministry of Education, Youth and Sports of the CR, Structure and character of bonding, properties and analysis of synthetic and natural molecular ensembles
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