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Synthesis of Substituted 2-Benzoylaminothiobenzamides and Their Ring Closure to Substituted 2-Phenylquinazoline-4-thiones
Department of Organic Chemistry, University of Pardubice, Čs. legií 565, 532 10 Pardubice, Czech Republic
Research Institute of Pharmacy and Biochemistry, Kouřimská 17, 130 60 Prague 3, Czech Republic
Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, 500 05 Hradec Králové, Czech Republic
* Author to whom correspondence should be addressed.
Received: 4 December 2000; in revised form: 6 March 2001 / Accepted: 23 March 2001 / Published: 31 March 2001
Abstract: Acylation of 2-aminothiobenzamide or 2-methylaminothiobenzamide with substituted benzoyl chlorides has been used to synthesise the corresponding 2-benzoylaminothiobenzamides whose subsequent sodium methoxide-catalysed ring closure gives the corresponding quinazoline-4-thiones. These compounds were characterised by means of their 1H- and 13C-NMR spectra. The preferred tautomeric form of selected compounds has been discussed on the basis of their 13C-NMR, IR and Raman spectra. It has been found that in the given medium 1-methyl-quinazoline-4-thiones undergo a replacement of the sulphur substituent by oxygen giving 1-methyl-quinazoline-4-ones. In strong acid media, 2-benzoylaminothiobenzamide is cyclised through its sulphur atom to give 2-phenylbenzo[d-1,3]thiazin-4-one.
Keywords: 2-Benzoylaminothiobenzamides; quinazoline-4-thiones; tautomerism; ring closure
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Hanusek, J.; Hejtmánková, L.; Kubicová, L.; Sedlák, M. Synthesis of Substituted 2-Benzoylaminothiobenzamides and Their Ring Closure to Substituted 2-Phenylquinazoline-4-thiones. Molecules 2001, 6, 323-337.
Hanusek J, Hejtmánková L, Kubicová L, Sedlák M. Synthesis of Substituted 2-Benzoylaminothiobenzamides and Their Ring Closure to Substituted 2-Phenylquinazoline-4-thiones. Molecules. 2001; 6(4):323-337.
Hanusek, Jiří; Hejtmánková, Ludmila; Kubicová, Lenka; Sedlák, Miloš. 2001. "Synthesis of Substituted 2-Benzoylaminothiobenzamides and Their Ring Closure to Substituted 2-Phenylquinazoline-4-thiones." Molecules 6, no. 4: 323-337.