An efficient one-pot synthesis of polyhydroquinoline derivatives via Hantzsch condensation using heterogeneous catalyst under solvent-free conditions

Abstract

An efficient Hantzsch condensation of polyhydroquinoline derivatives was reported via a fourcomponent coupling reaction of aldehydes, dimedone, ethyl acetoacetate and ammonium acetate in the presence of HClO 4 -SiO 2 under solvent-free conditions. Operational simplicity, use of an economically convenient catalyst, high yield, short reaction times are the key features of this protocol.

Bio-Catalysis in Multicomponent Reactions

“…Compared to some traditional methods [ 34 , 35 , 36 ], the above enzyme-catalyzed synthesis of 1,4-dihydropyridine (DHP) derivatives appears superior not only because the procedures are milder, simple in their operation and more environmentally friendly but, also, because they allow access to a wider variety of heterocycles in this category.…”

Efficient one‐pot synthesis of polyhydroquinoline derivatives through the Hantzsch condensation using IRMOF‐3 as heterogeneous and reusable catalyst

“…For this reason, the syntheses of the polyhydroquinoline compound has not only captivated attention but also represents an interesting research challenge to chemists 12 . Numerous methods have been reported for the structurally related synthesis of polyhydroquinoline derivatives and of the biologically importance associated with these compound, and there are many classical methods, as well as various catalysts, such as silica per chloric acid (HClO 4 ‐SiO 2 ) 13 , ionic liquid 14 , heteropoly acid, 15 iron (II) trifluoro acetate 16 , trimethyl silyl chloride (TMSCl), 17 HY‐zeolite, 18 Sc(OTf) 3 , Yb (OTf) 3 19 montmorillonite K‐10, 20 and silica‐supported sulfuric acid (SSA); each of the methods offers different advantages for the Hantzsch condensation but, at the same time, suffer from certain drawbacks such as longer reaction time, unsatisfactory yields, toxic catalysts, expensive catalysts, harsh reaction conditions, difficult workup, and nonreusable catalysts. Hence, in order to overcome these limitations, it is necessary to develop an efficient, cost‐effective, and ecofriendly protocol synthesis of polyquinoline derivatives.…”

Four-component one-pot synthesis of unsymmetrical polyhydroquinoline derivatives using 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate as a catalyst

“…Compounds of this type have also been used in a number of other therapeutic applications where they have exhibited neuroprotectant and platelet anti-aggregatory activity, as well as being used as cerebral anti-ischemic agents in the treatment of Alzheimer's disease and chemo-sensitizers in tumor therapy [24,25]. Several procedures have been reported for the preparation of polyhydroquinolines, including the use of microwave irradiation [26], sonication [27], and a variety of different catalysts [28][29][30][31][32][33][34][35][36].…”