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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

1, 2, 3 and 1,*
1 Department of Organic Chemistry, University of Pardubice, Čs. legií 565, 532 10 Pardubice, Czech Republic 2 Research Institute of Pharmacy and Biochemistry, Kouřimská 17, 130 60 Prague 3, Czech Republic 3 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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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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