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Thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution
2-(Alkyl(aryl)amino)thiazol-4(5H)-ones can regioselectively be prepared from monoalkyl(aryl)thioureas and maleimides. In solution, the former heterocycles exist in a tautomeric equilibrium with 2-(alkyl(aryl)imino)thiazolidin-4-ones and the substituent on the exocyclic nitrogen atom governs the rati...
| Autores principales: | , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
Beilstein-Institut
2016
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238611/ https://www.ncbi.nlm.nih.gov/pubmed/28144325 http://dx.doi.org/10.3762/bjoc.12.251 |
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| author | Pankova, Alena S Golubev, Pavel R Khlebnikov, Alexander F Ivanov, Alexander Yu Kuznetsov, Mikhail A |
| author_facet | Pankova, Alena S Golubev, Pavel R Khlebnikov, Alexander F Ivanov, Alexander Yu Kuznetsov, Mikhail A |
| author_sort | Pankova, Alena S |
| collection | PubMed |
| description | 2-(Alkyl(aryl)amino)thiazol-4(5H)-ones can regioselectively be prepared from monoalkyl(aryl)thioureas and maleimides. In solution, the former heterocycles exist in a tautomeric equilibrium with 2-(alkyl(aryl)imino)thiazolidin-4-ones and the substituent on the exocyclic nitrogen atom governs the ratio of these tautomers. Isomers with the alkyl group in the endocyclic position can be obtained from N-methyl(ethyl)thioureas. 2D NMR spectroscopy and DFT calculations rationalize experimental results. |
| format | Online Article Text |
| id | pubmed-5238611 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2016 |
| publisher | Beilstein-Institut |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-52386112017-01-31 Thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution Pankova, Alena S Golubev, Pavel R Khlebnikov, Alexander F Ivanov, Alexander Yu Kuznetsov, Mikhail A Beilstein J Org Chem Full Research Paper 2-(Alkyl(aryl)amino)thiazol-4(5H)-ones can regioselectively be prepared from monoalkyl(aryl)thioureas and maleimides. In solution, the former heterocycles exist in a tautomeric equilibrium with 2-(alkyl(aryl)imino)thiazolidin-4-ones and the substituent on the exocyclic nitrogen atom governs the ratio of these tautomers. Isomers with the alkyl group in the endocyclic position can be obtained from N-methyl(ethyl)thioureas. 2D NMR spectroscopy and DFT calculations rationalize experimental results. Beilstein-Institut 2016-11-29 /pmc/articles/PMC5238611/ /pubmed/28144325 http://dx.doi.org/10.3762/bjoc.12.251 Text en Copyright © 2016, Pankova et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
| spellingShingle | Full Research Paper Pankova, Alena S Golubev, Pavel R Khlebnikov, Alexander F Ivanov, Alexander Yu Kuznetsov, Mikhail A Thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution |
| title | Thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution |
| title_full | Thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution |
| title_fullStr | Thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution |
| title_full_unstemmed | Thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution |
| title_short | Thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution |
| title_sort | thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution |
| topic | Full Research Paper |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238611/ https://www.ncbi.nlm.nih.gov/pubmed/28144325 http://dx.doi.org/10.3762/bjoc.12.251 |
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