The reaction of 6‐aminopyrimidin‐4‐ones 1 with benzaldehydes 2 and β‐aminocrotononitrile 3 or benzoylacetonitrile 4 under microwave irradiation in dry media yields the 6‐cyano‐5,8‐dihydropyrido[2,3‐d]‐pyrimidinones 5a‐t. The structure of the synthesized compounds was determined on the basis of nmr measurements, especially by 1H,1H−, 1H,13C COSY, DEPT and NOESY experiments. In contrast with other pyrido‐[2,3‐d]pyrimidine derivatives, these compounds did not show any antifungal in vitro activity up to 250 μg/mL.
The free‐solvent multicomponent reaction under microwave irradiation of 6‐aminopyrimidin‐4(3H)‐ones (1) with dimedone (2) and N,N‐dimethylformamide dimethylacetal yields the pyrimido[4,5‐c]isoquinolinones (5a‐j). In this process, the intermediate of cyclization was isolated. The structure of the synthesized compounds was determined on the basis of nmr measurements, especially by 1H,1H‐,1H,13C COSY, and DEPT. These compounds showed antifungal in vitro activity particularly against dermatophytes.
The supramolecular structure of the title compound, C18H17ClN2O2, is determined by the intersection of two chains formed by N—H⋯O and N—H⋯N hydrogen bonds, forming a two‐dimensional sheet.
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