{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T05:16:49Z","timestamp":1736831809868,"version":"3.33.0"},"reference-count":25,"publisher":"International Union of Crystallography (IUCr)","issue":"7","license":[{"start":{"date-parts":[[2015,6,13]],"date-time":"2015-06-13T00:00:00Z","timestamp":1434153600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"},{"start":{"date-parts":[[2015,6,13]],"date-time":"2015-06-13T00:00:00Z","timestamp":1434153600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr E Cryst Commun","Acta Cryst E","Acta Cryst Sect E","Acta Crystallogr E","Acta Crystallogr Sect E","Acta Cryst E Cryst Commun","Acta Cryst Sect E Cryst Commun"],"published-print":{"date-parts":[[2015,7,1]]},"abstract":"<jats:p>The title compounds, 6-(2-hydroxybenzyl)-5<jats:italic>H<\/jats:italic>-thiazolo[3,2-<jats:italic>a<\/jats:italic>]pyrimidin-5-one, C<jats:sub>13<\/jats:sub>H<jats:sub>8<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>3<\/jats:sub>S, (<jats:bold>1<\/jats:bold>), and 6-(2-hydroxybenzyl)-3-methyl-5<jats:italic>H<\/jats:italic>-thiazolo[3,2-<jats:italic>a<\/jats:italic>]pyrimidin-5-one, C<jats:sub>14<\/jats:sub>H<jats:sub>10<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>3<\/jats:sub>S, (<jats:bold>2<\/jats:bold>), 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\u2014H...O hydrogen bond, which generates an<jats:italic>S<\/jats:italic>(6) ring. The dihedral angles between the heterocyclic moiety and the 2-hydroxybenzoyl ring are 55.22\u2005(5) and 46.83\u2005(6)\u00b0 for (<jats:bold>1<\/jats:bold>) and (<jats:bold>2<\/jats:bold>), respectively. In the crystals, the molecules are linked by weak C\u2014H...O hydrogen bonds and \u03c0\u2013\u03c0 stacking interactions.<\/jats:p>","DOI":"10.1107\/s2056989015011044","type":"journal-article","created":{"date-parts":[[2015,6,12]],"date-time":"2015-06-12T08:22:54Z","timestamp":1434097374000},"page":"766-771","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Crystal structures of two 6-(2-hydroxybenzoyl)-5<i>H<\/i>-thiazolo[3,2-<i>a<\/i>]pyrimidin-5-ones"],"prefix":"10.1107","volume":"71","author":[{"given":"Ligia R.","family":"Gomes","sequence":"first","affiliation":[]},{"given":"John Nicolson","family":"Low","sequence":"additional","affiliation":[]},{"given":"Fernando","family":"Cagide","sequence":"additional","affiliation":[]},{"given":"Fernanda","family":"Borges","sequence":"additional","affiliation":[]}],"member":"329","published-online":{"date-parts":[[2015,6,13]]},"reference":[{"key":"hb7437_bb1","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1016\/j.ejmech.2009.09.037","volume":"45","author":"Abd El-Galil","year":"2010","journal-title":"Eur J Med Chem."},{"key":"hb7437_bb2","doi-asserted-by":"crossref","first-page":"S1","DOI":"10.1039\/p298700000s1","volume":"2","author":"Allen","year":"1987","journal-title":"J. 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