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区域选择性的亲电攻击4-methyl-1-thioxo-1、2、4,5-tetrahydro(1、2、4)triazolo[4,3]quinazolin-5-one。.pdfVIP

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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区域选择性的亲电攻击4-methyl-1-thioxo-1、2、4,5-tetrahydro(1、2、4)triazolo[4,3]quinazolin-5-one。.pdf

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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区域选择性的亲电攻击4-methyl-1-thioxo-1、2、4,5-tetrahydro(1、2、4)triazolo[4,3]quinazolin-5-one。

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 1 1,2 1 Walid Fathalla , Michal Čajan and Pavel Pazdera* 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 2 derivatives followed by a transacylation reaction to give the N -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 spectro