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,* email
Received: 26 July 2000; in revised form: 20 October 2000 / Accepted: 10 November 2000 / Published: 15 December 2000
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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
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MDPI and ACS Style

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.

AMA Style

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(12):1210-1223.

Chicago/Turabian Style

Fathalla, W.; Čajan, M.; Pazdera, P. 2000. "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 5, no. 12: 1210-1223.

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