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Molecules 2000, 5(12), 1210-1223; doi:10.3390/51201210
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 2: Reactions on Nitrogen Atom

1, 1,2 and 1,*
1 Department of Organic Chemistry, Faculty of Science, Masaryk University, Brno, Czech Republic 2 Laboratory of Biomolecular Structure and Dynamics, Faculty of Science, Masaryk University, Brno, Czech Republic
* Author to whom correspondence should be addressed.
Received: 26 July 2000 / Revised: 20 October 2000 / Accepted: 10 November 2000 / Published: 15 December 2000
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Abstract

The regioselectivity on a cyclic thioamide group towards different electrophiles was studied on the model compound 4-methyl-1-thioxo-1,2,4,5-tetrahydro[1,2,4]triazolo [4,3-a]quinazolin-5-one 1. The examined compound 1 reacts with alkyl halides, amines in the presence of formaldehyde, acyl halides and compounds having activated double bonds to afford the N-substituted derivatives 2, 3 and 6. The regioselective reactions on nitrogen atom are due to strong Coulombic attraction. The reaction of 1 with amines in the presence of hydrogen peroxide afforded the aminolysis product 4. Compounds 1-6 were identified by FTIR, 1H NMR, 13C NMR, and mass spectroscopy.
Keywords: 4-methyl-1-thioxo-1; 2; 4; 5-tetrahydro[1; 2; 4]triazolo[4; 3-a]quinazolin-5-one; regioselective reactions; cyclic thioamides 4-methyl-1-thioxo-1; 2; 4; 5-tetrahydro[1; 2; 4]triazolo[4; 3-a]quinazolin-5-one; regioselective reactions; cyclic thioamides
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Fathalla, W.; Čajan, M.; Pazdera, P. 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 2: Reactions on Nitrogen Atom. Molecules 2000, 5, 1210-1223.

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