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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...

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Autores principales: Gomes, Ligia R., Low, John Nicolson, Cagide, Fernando, Borges, Fernanda
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
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.
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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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