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

Muchchintala Maheswara,Vidavalur Siddaiah,Chunduri Venkata Rao,Guri Lakishmi Vasantha Damu

doi:10.3998/ark.5550190.0007.223

Muchchintala Maheswara, Vidavalur Siddaiah + Show 2 more

Open Access

https://doi.org/10.3998/ark.5550190.0007.223

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Abstract

An efficient Hantzsch condensation of polyhydroquinoline derivatives was reported via a four- component coupling reaction of aldehydes, dimedone, ethyl acetoacetate and ammonium acetate in the presence of HClO4-SiO2 under solvent-free conditions. Operational simplicity, use of an economically convenient catalyst, high yield, short reaction times are the key features of this protocol.

Highlights

4-Substituted 1,4-dihydropyridines (1,4-DHPs) are well known as Ca2+ channel blockers and emerged as one of the most important classes of drugs for the treatment of cardiovascular diseases, including hypertension.1 1,4-Dihydropyridines possess a variety of biological activities, such as, vasodilator, bronchodilator, anti-atherosclerotic, antitumor, geroprotective, hepatoprotective and antidiabetic agent.2a-d Recent studies have revealed that 1,4-DHPs exhibit several medicinal applications which include neuroprotectant3a and platelet anti-aggregatory activity,3b in addition cerebral antiischemic activity in the treatment of Alzheimer’s disease3c and as chemo sensitizer in tumor therapy.3d These examples clearly demonstrate the remarkable potential of novel DHP derivatives as a source of valuable drug candidates
The synthesis of the heterocyclic nucleus is of continuing interest
HClO4-SiO2 has been used to catalyze the acetylation of alcohols and phenols using acetic acid.[21]

Summary

Introduction

4-Substituted 1,4-dihydropyridines (1,4-DHPs) are well known as Ca2+ channel blockers and emerged as one of the most important classes of drugs for the treatment of cardiovascular diseases, including hypertension.1 1,4-Dihydropyridines possess a variety of biological activities, such as, vasodilator, bronchodilator, anti-atherosclerotic, antitumor, geroprotective, hepatoprotective and antidiabetic agent.2a-d Recent studies have revealed that 1,4-DHPs exhibit several medicinal applications which include neuroprotectant3a and platelet anti-aggregatory activity,3b in addition cerebral antiischemic activity in the treatment of Alzheimer’s disease3c and as chemo sensitizer in tumor therapy.3d These examples clearly demonstrate the remarkable potential of novel DHP derivatives as a source of valuable drug candidates. In view of the importance of polyhydroquinoline derivatives, many classical methods for their synthesis were reported[8,9,10,11,12,13] using conventional heating and refluxing approaches in the presence of an organic solvent.

Results

Conclusion