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Molecules 2001, 6(4), 323-337; doi:10.3390/60400323

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 / Revised: 6 March 2001 / Accepted: 23 March 2001 / Published: 31 March 2001
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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 2-Benzoylaminothiobenzamides; quinazoline-4-thiones; tautomerism; ring closure
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

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.

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