Synthesis and biological application of pyranopyrimidine derivatives catalyzed by efficient nanoparticles and their nucleoside analogues

Abstract

Nanoparticles supply an environmentally friendly procedure for the synthesis of pyrano[2,3-d]pyrimidines by the one-pot three-component condensation reaction of thiobarbituric acid and malononitrile with pyrrol-2-carboxaldehyde. The catalyst could be easily recovered using an external magnet and reused for six cycles with almost consistent activity. A facile synthesis of a new series of cyclic and acyclic nucleosides of pyrano[2,3-d]pyrimidines derivatives was performed. The synthesis of poly heterocyclic compounds starting from pyrano[2,3-d]pyrimidines derivatives was achieved. Structures of the newly synthesized compounds were confirmed on the bases of elemental analyses and spectral data (IR, ¹H NMR, ¹³C NMR, and mass spectra). Compound 6 exhibited the most potent biological activity.

Graphical Abstract

Keywords:

• Hydrazonoyl chloride
• multicomponent reactions
• nanoparticles
• nucleosides
• polyheterocyclic
• pyrano[2,3-d]pyrimidine derivatives

Acknowledgments

The authors gratefully acknowledge the Central Laboratory of Medicine Ministry for performing the antimicrobial measurements and the Institute of Science and Nanotechnology in Kafr ElSheikh for synthesis of the nanoparticles (Mn₃O_4, Fe₃O₄, ZnO). A. F. El-Farargy thanks Professor Norbert Krause, Lehrstuhl für Organische Chemie, TU Dortmund, for his repeated invitations, kind hospitality, and the facilities offered.