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Synthesis of Substituted 2-Benzoylaminothiobenzamides and Their Ring Closure to Substituted 2-Phenylquinazoline-4-thiones
Acylation of 2-aminothiobenzamide or 2-methylaminothiobenzamide with substituted benzoyl chlorides has been used to synthesise the corresponding 2-benzoyl-aminothiobenzamides whose subsequent sodium methoxide-catalysed ring closure gives the corresponding quinazoline-4-thiones. These compounds were...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2001
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6236344/ http://dx.doi.org/10.3390/60400323 |
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author | Hanusek, Jiří Hejtmánková, Ludmila Kubicová, Lenka Sedlák, Miloš |
author_facet | Hanusek, Jiří Hejtmánková, Ludmila Kubicová, Lenka Sedlák, Miloš |
author_sort | Hanusek, Jiří |
collection | PubMed |
description | Acylation of 2-aminothiobenzamide or 2-methylaminothiobenzamide with substituted benzoyl chlorides has been used to synthesise the corresponding 2-benzoyl-aminothiobenzamides whose subsequent sodium methoxide-catalysed ring closure gives the corresponding quinazoline-4-thiones. These compounds were characterised by means of their (1)H- and (13)C-NMR spectra. The preferred tautomeric form of selected compounds has been discussed on the basis of their (13)C-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. |
format | Online Article Text |
id | pubmed-6236344 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2001 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62363442018-11-20 Synthesis of Substituted 2-Benzoylaminothiobenzamides and Their Ring Closure to Substituted 2-Phenylquinazoline-4-thiones Hanusek, Jiří Hejtmánková, Ludmila Kubicová, Lenka Sedlák, Miloš Molecules Article Acylation of 2-aminothiobenzamide or 2-methylaminothiobenzamide with substituted benzoyl chlorides has been used to synthesise the corresponding 2-benzoyl-aminothiobenzamides whose subsequent sodium methoxide-catalysed ring closure gives the corresponding quinazoline-4-thiones. These compounds were characterised by means of their (1)H- and (13)C-NMR spectra. The preferred tautomeric form of selected compounds has been discussed on the basis of their (13)C-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. MDPI 2001-03-31 /pmc/articles/PMC6236344/ http://dx.doi.org/10.3390/60400323 Text en © 2001 by MDPI (http://www.mdpi.org). Reproduction is permitted for noncommercial purposes |
spellingShingle | Article Hanusek, Jiří Hejtmánková, Ludmila Kubicová, Lenka Sedlák, Miloš Synthesis of Substituted 2-Benzoylaminothiobenzamides and Their Ring Closure to Substituted 2-Phenylquinazoline-4-thiones |
title | Synthesis of Substituted 2-Benzoylaminothiobenzamides and Their Ring Closure to Substituted 2-Phenylquinazoline-4-thiones |
title_full | Synthesis of Substituted 2-Benzoylaminothiobenzamides and Their Ring Closure to Substituted 2-Phenylquinazoline-4-thiones |
title_fullStr | Synthesis of Substituted 2-Benzoylaminothiobenzamides and Their Ring Closure to Substituted 2-Phenylquinazoline-4-thiones |
title_full_unstemmed | Synthesis of Substituted 2-Benzoylaminothiobenzamides and Their Ring Closure to Substituted 2-Phenylquinazoline-4-thiones |
title_short | Synthesis of Substituted 2-Benzoylaminothiobenzamides and Their Ring Closure to Substituted 2-Phenylquinazoline-4-thiones |
title_sort | synthesis of substituted 2-benzoylaminothiobenzamides and their ring closure to substituted 2-phenylquinazoline-4-thiones |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6236344/ http://dx.doi.org/10.3390/60400323 |
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