Application of novel nanomagnetic metal\u2013organic frameworks as a catalyst for the synthesis of new pyridines and 1,4-dihydropyridines via a cooperative vinylogous anomeric based oxidation

Saeed Babaee,Mohammad Ali Zolfigol,Hassan Sepehrmansourie,Mahmoud Zarei,Sadegh Rostamnia

doi:10.1038/s41598-021-84005-2

Abstract

Herein, a new magnetic metal–organic frameworks based on Fe3O4 (NMMOFs) with porous and high surface area materials were synthesized. Then, NMMOFs were characterized by FT-IR, XRD, SEM, elemental mapping, energy dispersive X-ray (EDS), TG, DTG, VSM, and N2 adsorption–desorption isotherms (BET). Fe3O4@Co(BDC)-NH2 as a magnetic porous catalyst was applied for synthesis of novel fused pyridines and 1,4-dihydropyridines with pyrazole and pyrimidine moieties as suitable drug candidates under ultrasonic irradiation. The significant advantages of the presented methodology are mild, facile workup, high yields, short reaction times, high thermal stability, and reusability of the described NMMOFs catalyst.

Highlights

A new magnetic metal–organic frameworks based on Fe3O4 (NMMOFs) with porous and high surface area materials were synthesized
Porous and magnetic materials have been widely used in biotechnology, magnetic resonance imaging (MRI), catalysis, adsorption, gas separation, and purification, optics, drug delivery, etc.[4,5,6]
A nanomagnetic metal–organic frameworks (NMMOFs) was designed, characterized and applied for the preparation of pyridines fused with pyrazole and pyrimidine under ultrasonic irradiation

Summary

Result and discussion

The systematic study of the stereoelectronic effects in target molecules, allows for the design of synthetic strategies based on a nomerically driven stereoselective reactions, or highly biased equilibria among isomeric products. The obtained results from this research will be supporting the idea of rational designs, syntheses, and applications of tasked-specific catalysts and molecules for the development of stereoelectronic effects in the course of organic synthesis With this aim, a nanomagnetic metal–organic frameworks (NMMOFs) was designed, characterized and applied for the preparation of pyridines fused with pyrazole and pyrimidine under ultrasonic irradiation. The obtained spectra are as same as the corresponding spectra of fresh catalyst (Figures S7, S8 see supporting information), to compare the performance of nanomagnetic metal–organic frameworks (NMMOFs) catalyst for the synthesis of desired fused pyridines and 1,4-dihydropyridines with pyrazole and pyrimidine moieties via a cooperative vinylogous anomeric based oxidation, we have used various organic and inorganic acid catalysts for condensation reaction between 4-nitro benzaldehyde (1.0 mmol, 0.151 g), 3-methyl-1-phenyl-1H-pyrazole-5-amine (1.0 mmol, 0.174 g) and pyrimidine-2,4,6(1H,3H,5H)-trione (1.0 mmol, 0.128 g).

Conclusion

H O R2 N