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A series of some novel pyrano [2,3-d]pyrimidine 4-10 with 75-95% yields and pyridino[2,3-d]pyrimidine derivatives 11-16 with 75-92% yields is reported. The building structures have been achieved by reaction of 5-arylidene barbituric acid 2 and active nucleophile carbon or nitrogen as examples barbituric acid and acetyl acetone or refluxing of bispyrimidine-2,4,6-trione derivative 3 with cyclizing reagents such as phosphorous pentoxide, hydrazine hydrate and aminothiazole. The newly synthesized structures have been elucidated on the basis of their spectral analysis. Some selected members were screened for antitumor activity. Among the screened compounds 9, 16, 7, 10 and 8 exhibited high antitumor activity.

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Based on sequential organic transformations, that is, diimine formation, Staudinger [2 + 2] ketene–imine cycloaddition, and ring-closing metathesis (RCM) reactions, the synthesis with full structural identification including NMR and HRMS spectral data along with single X-ray diffraction analysis (for anti 7b, anti 8b, syn 9a, and anti 9b) of the first syn/anti bis-4-spiro-β-lactams-based azacrown ethers (7a,b–9a,b) is reported.

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