A facile and efficient synthesis of 1,8-dioxodecahydroacridines derivatives catalyzed by cobalt\u2013alanine metal complex under aqueous ethanol media

M Mujahid Alam,Ahmed M Fouda,Ahmed T Mubarak,Mohammed A Assiri,S Merajuddin Ahmed

doi:10.1186/s13065-019-0545-3

Abstract

A facile and convenient method for the synthesis of acridines and its derivatives was developed through one-pot, three-component condensation reaction of aromatic aldehydes, 5,5-dimethyl-1,3-cyclohexanedione, aryl amines or ammonium acetates in the presence of a catalytic amount of cobalt–alanine metal complex using aqueous ethanol as a reaction medium is reported. The present described novel methodology offers several advantages over the traditional methods reported in the literature, such as mild reaction conditions, inexpensive catalyst, short reaction times, excellent yields of products, simplicity and easy workup are the advantages of this procedure.

Highlights

Multi-component reactions (MCRs) have been paid much attention by synthetic organic chemists worldwide due to the effectiveness of multiple component reactions at building functionalized, novel drug discovery procedures and allow the fast, automated and highthroughput generation of organic compounds [1]
Initially, we studied the one-pot three component condensation reaction of benzaldehyde (1 mmol), dimedone (2 mmol) and aniline (1 mmol) as a model reaction in the presence of cobalt–alanine complex (5 mol%) as a catalyst in aqueous ethanol solvent system and the product was obtained in excellent yield (Scheme 1)
After successful of the model reaction, we studied for the optimization of the reaction conditions with respect to temperature, time, solvent and molar ratio of the catalyst

Summary

Introduction

Multi-component reactions (MCRs) have been paid much attention by synthetic organic chemists worldwide due to the effectiveness of multiple component reactions at building functionalized, novel drug discovery procedures and allow the fast, automated and highthroughput generation of organic compounds [1]. Acridine-1,8-dione and acridine derivatives are well known polyfunctionalized 1,4-dihydropyridines (DHPs) [12] These derivatives of DHPs have an important ring skeleton and reported wide range of pharmaceutical and biological properties, including antitumor [13], antitubercular [14], antimalaria [15], antibacterial [16], antihypertensive [17], fungicidal [18], anticancer [19], anti-inflammatory [20] and diabetes [21]. These derivatives are commercially used as calcium channel blockers [22,23,24]. These derivatives have the applications in material science like semiconductors [38] and in spectroscopy as luminescent agent [39]

Methods

Results

Conclusion