Synthesis and Application of Imidazolium-Based Ionic Liquid Supported on Hydroxyapatite Encapsulated γ-Fe₂O₃ Nanocatalyst in Preparation of Pyrido[2,3-d]Pyrimidines

Abstract

Synthesis of novel 2-amino-5-aryl-7-(1-methyl-1H-pyrrol-2-yl)-4-oxo-3,4,5,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carbonitrile derivatives is reported by the reaction of 2,6-diaminopyrimidin-4(3H)-one, 3-(1-methy-1H-pyrrol-2-yl)-3-oxopropane nitrile and aryl aldehydes in the presence of newly synthesized imidazolium based ionic liquid supported on hydroxyapatite encapsulated γ-Fe₂O₃ nanocatalyst [γ-Fe₂O₃@HAp-Si(CH₂)₃Cl@DMIM] in short reaction times (7-13 min) and high to excellent yields (80%–95%). Cleaner reaction profile, mild reaction conditions, use of the green solvent and reusability of the catalyst, make this protocol attractive for the large scale synthesis of pyrido[2,3-d]pyrimidine-6-carbonitrile derivatives and is amenable for iterative combinatorial library generation. The synthesized nanoparticles were characterized by Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscope, energy dispersive analysis of X-rays, thermogravimetric analysis, differential thermogravimetric and vibrating sample magnetometer.

Graphical abstract

A novel imidazolium based ionic liquids supported on hydroxyapatite encapsulated γ-Fe₂O₃ nanocatalyst [γ-Fe₂O₃@HAp-Si(CH₂)₃Cl@DMIM] was synthesized and used in a practical and efficient synthesis of new 2-amino-5-aryl-7-(1-methyl-1H-pyrrol-2-yl)-4-oxo-3,4,5,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carbonitrile derivatives.

Keywords:

• 12-Dimethylimidazole
• γ-Fe₂O₃
• HAp
• ionic liquid
• magnetic nanocatalyst
• pyrido[23-d]pyrimidines
• pyrrole

Disclosure statement

No potential conflict of interest was reported by the authors.