Regioselectivity of Electrophilic Attack on 4-Methyl-1-Thioxo-1,2,4,5-Tetrahydro1,2,4Triazolo4,3-AQuinazolin-5-One Part 2: Reactions on Nitrogen AtomReport as inadecuate


Regioselectivity of Electrophilic Attack on 4-Methyl-1-Thioxo-1,2,4,5-Tetrahydro1,2,4Triazolo4,3-AQuinazolin-5-One Part 2: Reactions on Nitrogen Atom


Regioselectivity of Electrophilic Attack on 4-Methyl-1-Thioxo-1,2,4,5-Tetrahydro1,2,4Triazolo4,3-AQuinazolin-5-One Part 2: Reactions on Nitrogen Atom - Download this document for free, or read online. Document in PDF available to download.

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





*

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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-tetrahydro1,2,4triazolo 4,3-aquinazolin-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. View Full-Text

Keywords: 4-methyl-1-thioxo-1; 2; 4; 5-tetrahydro1; 2; 4triazolo4; 3-aquinazolin-5-one; regioselective reactions; cyclic thioamides 4-methyl-1-thioxo-1; 2; 4; 5-tetrahydro1; 2; 4triazolo4; 3-aquinazolin-5-one; regioselective reactions; cyclic thioamides





Author: W. Fathalla 1, M. ńĆajan 1,2 and P. Pazdera 1,*

Source: http://mdpi.com/



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