Microporous hierarchically Zn-MOF as an efficient catalyst for the Hantzsch synthesis of polyhydroquinolines

Sayed Mohammad Ramish,Arash Ghorbani-Choghamarani,Masoud Mohammadi

doi:10.1038/s41598-022-05411-8

Sayed Mohammad Ramish, Arash Ghorbani-Choghamarani + Show 1 more

Open Access

https://doi.org/10.1038/s41598-022-05411-8

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Journal: Scientific Reports	Publication Date: Jan 27, 2022
Citations: 48	License type: open-access

Affiliation: Ilam University, Bu-Ali Sina University

Abstract

A three-dimensional walnut-like Zn-based MOF microsphere system was designed and synthesized via hydrothermal reaction of zinc salt with 4,6-diamino-2-pyrimidinethiol as a tridentate ligand. Besides, Zn ions were coordinated to the functional groups of the ligand to give a novel Zn-MOF microsphere material. Afterward, the resultant material was thoroughly characterized using various analysis and physico-chemical methods; including, FT-IR, XRD, TGA, EDX, X-ray mapping, SEM, TEM, and BET analysis. The Zn-MOF microspheres were utilized in the Hantzsch reaction for a selective synthesis of asymmetric polyhydroquinolines, using various aromatic aldehydes. Our strategy aims at providing a controlled synthesis of hierarchically nanoporous Zn-MOF microspheres with a well-defined morphology, structure, and excellent catalytic properties. Besides, it would result in having a promising heterogeneous catalyst for a selective synthesis with good yields, short reaction time, a low limit of steric hindrance and electronic effects. Moreover, the heterogeneity of the catalyst is further tested with hot filtration and also the reusability results point.

Highlights

Porous materials with large specific surface areas and other unique properties have gained increasing attention[1,2,3]
We propose to develop a novel selective heterogeneous catalytic system for the recognition of the polyhydroquinoline derivatives to facilitate the screening of the catalysts for this asymmetric reaction
We found out that Zn-Metal–organic frameworks (MOFs) can be used as a rapid catalyst to synthesize the polyhydroquinolines with excellent yields

Summary

Introduction

Porous materials with large specific surface areas and other unique properties have gained increasing attention[1,2,3]. We studied the hydrothermal synthesis of novel Zn-based nanoporous microspheres, by the reaction of zinc nitrate hexahydrate salt with 4,6-Diamino-2-pyrimidinethiol containing amine, thiol, and pyrimidine functional groups. This study reports the synthesis of nanoporous Zn-MOF microspheres to develop an efficient and novel heterogeneous catalyst to synthesize polyhydroquinolines as an important dihydropyridine-containing scaffold via Hantzsch reaction.

Results

Conclusion