A Set of phenyl sulfonate metal coordination complexes triggered Biginelli reaction for the high efficient synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones under solvent‐free conditions

Abstract

Three new metal coordination complexes, namely, [Co (DPE)(H2O)4](DPE)(BS)2 (1), [Co (DPE)2(H2O)4](ABS)2 (2), [Co (DPE)(H2O)4](MBS)2(CH3OH)2 (3) [DPE = (E)‐1,2‐di (pyridin‐4‐yl) ethene, BS = phenyl sulfonic acid, ABS = p‐aminobenzene sulfonic acid, MBS = p‐methylbenzene sulfonic acid] were obtained under hydrothermal conditions. Complexes 1‐3 were structurally characterized by X‐ray single‐crystal diffraction, powder X‐ray diffraction and IR. Complexes 1 and 3 exhibit a one‐dimensional chain structure, and complex 2 does a zero‐dimensional one. These three complexes further generate a three‐dimensional supramolecular architecture via strong hydrogen bonding interactions and packing interactions. These three metal coordination complexes show high catalytic performance for green synthesis of a variety of 3,4‐dihydropyrimidin‐2(1H)‐ones through the Biginelli reactions, which show several advantages such as excellent yields, short reaction times, eco‐friendly synthesis conditions, and simple isolated workup procedure. Interestingly, the order of catalytic activities for these catalysts is the following: 3>1>2, which can be ascribed to the acidities and hydrophobic interactions of phenyl sulfonate groups.

Asparagine-EDTA MNPs: A Highly Efficient And Recyclable Magnetic Multifunctional Core-Shell Nanocatalyst For Green Synthesis of Biologically-Active 3,4-Dihydropyrimidin-2(1H)-One Compounds

“…Among the various types of nitrogen-containing heterocycles, derivatives of 3,4-dihydropyrimidin-2(1H)one, as biologically-active compounds, have found versatile applications such as anti-bacterial, anti-in ammatory, antihypertensive agents, calcium channel blockers, antitumor compounds [41][42][43][44][45][46][47] . A simple and general protocol for access to 3,4-dihydropyrimidin-2(1H)-ones involves a three-component one-pot Biginelli cyclocondensation of ethyl acetoacetate, urea and various aldehydes accelerated by different types of catalytic systems such as polymer-supported catalysts 48 , ionic liquids 49,50 , ionic liquid/silica sulfuric acid 51 , metal−organic framework (MOF) 52,53 , montmorillonite clay 54 , magnetic nanoparticles 55 , Lewis acidic zirconium (IV)-salophen per uorooctanesulfonate or sulfated polyborate 56,57 , nanocrystalline CdS thin lm 46 , graphene oxide 58,59 and mesoporous materials 60,61 as well as environmental friendly energy inputs such as ultrasound 62 or microwave irradiation 63 . Most of the reported methods in this regard have the role of heterogeneous catalysts and high value.…”

Biochar-Based Graphitic Carbon Nitride Adorned with Ionic Liquid Containing Acidic Polymer: A Versatile, Non-Metallic Catalyst for Acid Catalyzed Reaction

“…Hence, many catalytic systems have been improved for the synthesis of DHPMs, including magnetic catalysts [ 41 , 42 , 43 ], ionic liquids [ 44 , 45 , 46 ], carbohydrate [ 47 , 48 ], Bronsted acids [ 49 , 50 , 51 ] and Lewis acid [ 52 , 53 , 54 ]. On the other hand, the importance of this reaction lies in the biological properties of DHPMs and wide utility for pharmaceutical purposes, such as antiviral, antimalarial, antihypertensive, antifungal, antitubercular and antibacterial properties [ 55 , 56 , 57 ]. This multicomponent reaction is mostly promoted by an appropriate catalyst [ 58 , 59 , 60 , 61 ].…”