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Authors = Michal Čajan

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14 pages, 226 KiB  
Article
One-Pot Quinazolin-4-ylidenethiourea Synthesis via N-(2-Cyanophenyl)benzimidoyl isothiocyanate
by Walid M. Fathalla, Michal Čajan, Jaromír Marek and Pavel Pazdera
Molecules 2001, 6(7), 574-587; https://doi.org/10.3390/60700574 - 30 Jun 2001
Cited by 23 | Viewed by 7811
Abstract
1,1-Disubstituted-3-(2-phenyl-3H-quinazolin-4-ylidene)thioureas (8) were synthesized in a one pot reaction of N-(2-cyanophenyl)benzimidoyl isothicyanate (3) with secondary amines. The products underwent transamination reactions. Compounds 8a-8g were identified by FTIR, 1H-NMR, 13C-NMR, mass spectroscopy and X-ray crystallography. Full article
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17 pages, 180 KiB  
Article
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
by Walid Fathalla, Michal Čajan and Pavel Pazdera
Molecules 2001, 6(6), 557-573; https://doi.org/10.3390/60600557 - 31 May 2001
Cited by 37 | Viewed by 7484
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 [...] Read more.
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. Full article
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