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

• Type: Article in International Scientific Journal
• Date: 2015

Authors

Gomes, LR (Author) Other; Low, JN (Author) Other; Fernando Cagide (Author) FCUP; Fernanda Borges (Author) FCUP

Journal

Title: Acta Crystallographica Section E: Crystallographic Communications

Vol. 71

Pages: 766-+

Publisher: International Union of Crystallography

Indexing

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Other information

Authenticus ID: P-00H-RM8

DOI: 10.1107/s2056989015011044

Abstract (EN): 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 center dot center dot center dot 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)degrees for (1) and (2), respectively. In the crystals, the molecules are linked by weak C-H center dot center dot center dot O hydrogen bonds and pi-pi stacking interactions.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 14