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Crystal structures of two 6-(2-hydroxybenzoyl)-5H-thiazolo[3,2-a]pyrimidin-5-ones
The title compounds, 6-(2-hydroxybenzyl)-5H-thiazolo[3,2-a]pyrimidin-5-one, C(13)H(8)N(2)O(3)S, (1), and 6-(2-hydroxybenzyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one, C(14)H(10)N(2)O(3)S, (2), were synthesized when a chromone-3-carboxylic acid, activated with (benzotriazol-1-yloxy)tripy...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4518966/ https://www.ncbi.nlm.nih.gov/pubmed/26279863 http://dx.doi.org/10.1107/S2056989015011044 |
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author | Gomes, Ligia R. Low, John Nicolson Cagide, Fernando Borges, Fernanda |
author_facet | Gomes, Ligia R. Low, John Nicolson Cagide, Fernando Borges, Fernanda |
author_sort | Gomes, Ligia R. |
collection | PubMed |
description | The title compounds, 6-(2-hydroxybenzyl)-5H-thiazolo[3,2-a]pyrimidin-5-one, C(13)H(8)N(2)O(3)S, (1), and 6-(2-hydroxybenzyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one, C(14)H(10)N(2)O(3)S, (2), were synthesized when a chromone-3-carboxylic acid, activated with (benzotriazol-1-yloxy)tripyrrolidinylphosphonium hexafluoridophosphate (PyBOP), was reacted with a primary heteromamine. Instead of the expected amidation, the unusual title thiazolopyrimidine-5-one derivatives were obtained serendipitously and a mechanism of formation is proposed. Both compounds present an intramolecular O—H⋯O hydrogen bond, which generates an S(6) ring. The dihedral angles between the heterocyclic moiety and the 2-hydroxybenzoyl ring are 55.22 (5) and 46.83 (6)° for (1) and (2), respectively. In the crystals, the molecules are linked by weak C—H⋯O hydrogen bonds and π–π stacking interactions. |
format | Online Article Text |
id | pubmed-4518966 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-45189662015-08-14 Crystal structures of two 6-(2-hydroxybenzoyl)-5H-thiazolo[3,2-a]pyrimidin-5-ones Gomes, Ligia R. Low, John Nicolson Cagide, Fernando Borges, Fernanda Acta Crystallogr E Crystallogr Commun Research Communications The title compounds, 6-(2-hydroxybenzyl)-5H-thiazolo[3,2-a]pyrimidin-5-one, C(13)H(8)N(2)O(3)S, (1), and 6-(2-hydroxybenzyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one, C(14)H(10)N(2)O(3)S, (2), were synthesized when a chromone-3-carboxylic acid, activated with (benzotriazol-1-yloxy)tripyrrolidinylphosphonium hexafluoridophosphate (PyBOP), was reacted with a primary heteromamine. Instead of the expected amidation, the unusual title thiazolopyrimidine-5-one derivatives were obtained serendipitously and a mechanism of formation is proposed. Both compounds present an intramolecular O—H⋯O hydrogen bond, which generates an S(6) ring. The dihedral angles between the heterocyclic moiety and the 2-hydroxybenzoyl ring are 55.22 (5) and 46.83 (6)° for (1) and (2), respectively. In the crystals, the molecules are linked by weak C—H⋯O hydrogen bonds and π–π stacking interactions. International Union of Crystallography 2015-06-13 /pmc/articles/PMC4518966/ /pubmed/26279863 http://dx.doi.org/10.1107/S2056989015011044 Text en © Gomes et al. 2015 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/ |
spellingShingle | Research Communications Gomes, Ligia R. Low, John Nicolson Cagide, Fernando Borges, Fernanda Crystal structures of two 6-(2-hydroxybenzoyl)-5H-thiazolo[3,2-a]pyrimidin-5-ones |
title | Crystal structures of two 6-(2-hydroxybenzoyl)-5H-thiazolo[3,2-a]pyrimidin-5-ones |
title_full | Crystal structures of two 6-(2-hydroxybenzoyl)-5H-thiazolo[3,2-a]pyrimidin-5-ones |
title_fullStr | Crystal structures of two 6-(2-hydroxybenzoyl)-5H-thiazolo[3,2-a]pyrimidin-5-ones |
title_full_unstemmed | Crystal structures of two 6-(2-hydroxybenzoyl)-5H-thiazolo[3,2-a]pyrimidin-5-ones |
title_short | Crystal structures of two 6-(2-hydroxybenzoyl)-5H-thiazolo[3,2-a]pyrimidin-5-ones |
title_sort | crystal structures of two 6-(2-hydroxybenzoyl)-5h-thiazolo[3,2-a]pyrimidin-5-ones |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4518966/ https://www.ncbi.nlm.nih.gov/pubmed/26279863 http://dx.doi.org/10.1107/S2056989015011044 |
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