A Novel Cascade Reaction of Aryl Aldoxime with Dimedone Under Microwave Irradiation: The Synthesis ofN-Hydroxylacridine

Abstract

A novel sequential addition, elimination and cyclization reactions took place when aldoxime and dimedone in glycol was subjected to microwave irradiation and a new type of N-hydroxylacridinedione derivatives was obtained in excellent yields (80-95%) within a short reaction time (4-8 min).

SiO2/ZnCl2-Catalyzed Heterocyclic Synthesis: Green, Rapid and Efficient One-Pot Synthesis of 14-H-dibenzo [a, j]Xanthenes, 1,8-Dioxo-octahydroxanthenes and 1,8-Dioxo-Decahydroacridines Under Solvent-Free Conditions

“…Also by comparison of their physical and spectroscopic data with those of authentic samples [27][28][29][30][31][32] .…”

Mg(BF4)2 doped in [BMIm][BF4]: A homogeneous ionic liquid-catalyst for efficient synthesis of 1,8-dioxo-octahydroxanthenes, decahydroacridines and 14-aryl-14H-dibenzo[a,j]xanthenes

“…1,4-Dihydropyridines represent an important class of compounds which are found in many sorts of biologically active compounds such as vasodilators, bronchodilators, antiatherosclerotics, antitumors, geroprotectives, hepatoprotective agents [29], and calcium channel blockers [30,31]. 1,8-Dioxodecahydroacridines with inbuilt 1,4-dihydropyridine nucleus have shown very high lasing efficiencies [32] and hence used as photoinitiators [33]. As a consequence of these interesting properties, a large library of acridinediones has been synthesized by the reaction of aldehydes with 2 equivalents of 1,3-cyclohexanedione or 5,5-dimethyl-1,3-cyclohexanedione and appropriate amines via various methods [34][35][36][37][38].…”

Study on one-pot four-component synthesis of 9-aryl-hexahydro-acridine-1,8-diones using SiO2–I as a new heterogeneous catalyst and their anticancer activity

“…7 Acridines have also received significant attention from many pharmaceutical and organic chemists, essentially because of the broad spectrum of their biological and pharmaceutical properties, such as: antiviral, 8 antibacterial, 9 anti-nociceptive activities, 10 as well as efficiency in photodynamic therapy 11 and because of the anti-inflammatory activity. 12 There are a few reports in the literature on the three-component Hantzsch-type condensation of aromatic aldehydes, anilines and dimedone via the traditional heating in organic solvents 13,14 under microwave irradiation 15 and in ionic liquids 16,17 leading to acridines. The main drawback of these methods is the inability to synthesize 9-aryl-hexahydroacridine-1,8-diones, therefore, the development of simple, efficient, high-yielding and environment friendly methods and use of simple, readily available, recyclable, new heterogeneous catalysts for the preparation of acridines under mild conditions is in demand.…”