Crystal structures of two 6-(2-hy­droxy­benzo­yl)-5H-thia­zolo[3,2-a]pyrimidin-5-ones

Acta Crystallographica Section E: Crystallographic Communications

Low, J.N.³  Gomes, L.R.⁴  Cagide, F.⁵  Borges, F.^1,11 

[1]CIQUP/Departamento de Quí

[2]Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland

[3]ENAS–

[4]FP–

[5]Faculdade de Ciê

[6]REQUIMTE/Departamento de Quí

[7]de da UFP, Universidade Fernando Pessoa, Rua Carlos da Maia, 296, P-4200-150 Porto, Portugal

[8]de, Escola Superior de Saú

[9]mica e Bioquí

[10]mica, Faculdade de Ciê

[11]ncias de Saú

[12]ncias, Universidade do Porto, 4169-007 Porto, Portugal

关键词: CRYSTAL STRUCTURE;    THIAZOLE;    CONFORMATION;    SUPRAMOLECULAR STRUCTURE;    HYDROGEN BONDING;    [PI]-[PI] STACKING INTERACTIONS;   

DOI  :  10.1107/S2056989015011044

学科分类：数学（综合）

来源: International Union of Crystallography

【 摘 要 】

The title compounds, 6-(2-hy­droxy­benz­yl)-5H-thia­zolo[3,2-a]pyrimidin-5-one, C13H8N2O3S, (1), and 6-(2-hy­droxy­benz­yl)-3-methyl-5H-thia­zolo[3,2-a]pyrimidin-5-one, C14H10N2O3S, (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.

【 授权许可】

CC BY