A Highly Chemically Robust 3D Interpenetrated MOF Heterogeneous Catalyst for the Synthesis of Hantzsch 1,4‐Dihydropyridines and Drug Molecules

Abstract

Metal–organic frameworks (MOFs) have attracted immense attention as efficient heterogeneous catalysts over other solid catalysts, however, their chemical environment instability often limits their catalytic potential. Herein, utilizing a flexible unexplored tetra‐acid ligand and employing the mixed ligand approach, a 3D interpenetrated robust framework is strategically developed, IITKGP‐51 (IITKGP stands for Indian Institute of Technology Kharagpur), which retained its crystallinity over a wide range of pH solution (4–12). Having ample open metal sites (OMSs), IITKGP‐51 is explored as a heterogeneous catalyst in one‐pot Hantzsch condensation reaction, with low catalyst loading for a broad range of substrates. The synthesis of drug molecules remains one of the most significant and emergent areas of organic and medicinal chemistry. Considering such practical utility, biologically important Nemadipine B and Nifedipine drug molecules (calcium channel protein inhibitor) are synthesized for the first time by using this catalyst and fully characterized via SC‐XRD and other spectroscopic methods. This report inaugurates the usage of a MOF material as a catalyst for the synthesis of drug molecules.

Coordinatively unsaturated 5-nitroisophthalate based cobalt(ii) coordination polymers: efficient catalytic CO2 fixation and Hantzsch condensation

“…The electron-withdrawing group-containing substrates (Table 4, 2d–h ) show relatively higher conversion in comparison to electron donating group-containing substrates (Table 4, 2b–c ) due to their electron-withdrawing influence at the rate-determining step in the nucleophilic addition reaction. 56,57…”

Novel BODIPY-based MOFs toward high-efficiency photocatalytic oxidation of sulfides and arylboronic acids

“…The 6-fold interpenetrated architecture of compound 1 might facilitate its stability. 35–37 Moreover, owing to the dramatic interpenetration, the total solvent-accessible space is merely 3.5% of the whole crystal volume (115.1 Å 3 out of the 3294.0 Å 3 per unit cell volume) as determined by PLATON 38 analysis. Overall, by simplification of Zn II to 4-connected nodes, the topology of 1 is related to an sra net with point symbol (4 2 ·6 3 ·8) (Fig.…”

Two-Dimensional Cu(II)-MOF with Lewis Acid–Base Bifunctional Sites for Chemical Fixation of CO2 and Bioactive 1,4-DHP Synthesis via Hantzsch Condensation

“…It may be noted that until now, only a single MOF has been used as a heterogeneous catalyst for the synthesis of any kind of drug molecules. However, the use of toxic Cd-center as a catalytically active site and the possibility of diffusion limitation through the three-dimensional channels could restrict the wide usage of the 3D MOF as a catalyst . On the contrary, the 2D framework with exposed catalytically active sites and the usage of environmentally benign copper metal as the catalytically active center; thus, extended the potential of the developed IITKGP-40 catalyst toward 1,4-DHP-based drug molecules synthesis.…”

“…Although taking advantage of several superior properties, MOFs have been explored in different catalytic transformations, the use of MOFs for synthesizing pharmacologically and biologically necessary medicinal compounds is mostly unexplored and thus demands enormous attention from the scientific community. To be precise, despite having a rich library of MOF-based solid catalysts, until now, only a single MOF has been reported as a catalyst for the synthesis of drug molecules, which signifies the importance of the exploration of newly developed MOF catalysts toward this direction …”