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 英文参考文献.docVIP

Molecules 2001, 6, 557-573 molecules ISSN 1420-3049 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 Walid Fathalla , Michal ?ajan and Pavel Pazdera* 1 1,2 1 1 Department of Organic Chemistry, Faculty of Science, Masaryk University, Brno, Czech Republic. Tel.: +420 5 Fax: +420 5 2 National Center for Biomolecular Research, Faculty of Science, Masaryk University, Brno, Czech Republic. *Author to whom correspondence should be addressed; E-mail: pazdera@chemi.muni.cz Received: 16 July 2000; in revised form 21 May 2001 / Accepted: 23 May 2001 / Published: 31 May 2001 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 N -acyl derivatives as 2 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. Keywords: Cyclic thioamides, regioselective reactions, 4-methyl-1-thioxo- 1,2,4,5-tetrahydro[1,2,4]triazolo[4,3-a]quinazolin-5-one, studies. DFT computational  Molecules 2001, 6 558 Introduction The thioamide group is an interesting system for heterocyclic chemists because it can be used as a useful synthetic building bloc, and its regioselectivity towards different electrophiles gives the group of the great importance.