Abstract

A simple and fastthree-component synthesis of new and biologically active hexahydro-2-quinolinecarboxylic acid scaf-fold 4 was carried out using cyclocondensation reaction of arylmethylidenepyruvic acids 1, 1,3-cyclohexandiones 2 and ammonium acetate 3 under solvent-free conditions and at room temperature. This protocol has the advantages of facility, easy work-up, high yields, short reaction time and environmentally friendly character.

Highlights

  • Heterocyclic containing nitrogen atom in their skeleton, are abundant in nature and exhibit various important chemical and biological activities

  • A simple and fastthree-component synthesis of new and biologically active hexahydro-2-quinolinecarboxylic acid scaffold 4 was carried out using cyclocondensation reaction of arylmethylidenepyruvic acids 1, 1,3-cyclohexandiones 2 and ammonium acetate 3 under solvent-free conditions and at room temperature

  • We report a very simple, efficient and clean synthetic route to 5-oxo-4-phenyl-1,4,5,6,7,8-hexahydro-2quinolinecarboxylic acid derivatives via three-component reaction of arylmethylidenepyruvic acids, 1,3-cyclohexandiones and ammonium acetate in solvent-free reaction condition

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Summary

Introduction

Heterocyclic containing nitrogen atom in their skeleton, are abundant in nature and exhibit various important chemical and biological activities. Among them quinolones are of interest because they constitute an important class of natural and non-natural products, many of which have different biological activities such as antimalarial[1], antibacterial[2], antimicrobial[3], and antistaphylococcal activities[4]. An important class of antibiotics possess 4-quinolone framework in their structure [5]. They can be used as useful drugs for the treatment of Alzheimer’s disease [6]. Kumar et al showed that some compounds with quinolone skeleton act as a lead in the antidiabetic discovery [7], with effects such as glycologenphosphorylase inhibitors [8,9,10,11,12], or as lipid lowering agent [13] and for the treatment of metabolic disorder. A number of quinolones are useful in industry as pigments [14]

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