One-pot Synthesis of 10-Methyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione Derivatives under Microwave Heating without Catalyst

Abstract

A series of 10-methyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione derivatives were synthesized by one-pot reaction of aldehyde, dimedone or 1,3-cyclohexanedione and methylamine in glycol or water under microwave heating without catalyst. The method has the advantage of short routine and reaction time, high yields as well as friendly environment. And the reaction was not only suitable for aliphatic and aromatic monoaldehyde, but also for aromatic dialdehyde.Keywords aldehyde, dimedone, 1, 3-cyclohexanedione, methylamine, 10-methyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione, microwave heating IntroductionDye lasers with an electrochemical control of radiation parameters have been shown to achieve stimulated emission in a broader spectral region.1 Among them, 10-methyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione dyes with heterocyclic structure have attracted much attention, due to their very high lasing efficience. 2,3 In virtue of the bichromophoric structure incorporating both the heterocyclic nitrogen and the carbonyl groups, these dyes have been revealed to act not only as electron donors but also electron acceptors 4-6 in the photoinitiated polymerization 7 of acrylates and methacrylates. They are also receiving much attention due to their likeness in properties with those of 1,4-dihydropyridines, which have similarities in structure to the biologically important compounds such as NADH and NADPH. 9 Furthermore, their method required two step reactions and complex operation.3 Therefore, it is necessary to develop an efficient and environmentally friendly synthesis for this kind of compounds.Since Gedye in 1986 used microwave heating for organic synthesis, 10 the microwave assisted organic synthesis has been a topic of continuing interest. 11 The application of microwave heating as a non-conventional energy source to activation of reactions, has now gained extensive usage, as it could lead to shorter reaction rates, higher yields, easier work-up and short reaction time. In our previous study, 12-14 we have synthesized large amounts of heterocyclic compounds by one-pot under microwave irradiation without catalyst. Through further investigation, we found that one-pot synthesis of 10-methyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-diones from aldehyde, dimedone or 1,3-cyclohexanedione and methylamine under microwave heating without catalyst could be successfully achieved in excellent yields and short reaction time. Herein, we would like to report this facile and efficient method, which is, to the best of our knowledge, the first one-pot synthesis of 10-methyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-diones from cheap reagents under microwave heating without catalyst. Results and discussionWith the aim of comparison, the reaction was carried out not only under microwave irradiation (Scheme 1) 2,3,4,5,6,7,8,9, Chin.

Microwave-Assisted Synthesis in Water as Solvent

“…The Hantzsch-related one-pot synthesis of N -substituted acridine derivatives 72 by condensation of an aldehyde, 2 equiv of 1,3-cyclohexanedione, and methylamine under open-vessel reflux conditions in a domestic microwave oven was reported by Tu and co-workers (Scheme ) . When 1,3-cyclohexanedione is employed as dicarbonyl substrate, water was used as solvent.…”

Synthesis, Characterization, and In Vitro Antimicrobial and Antifungal Activity of Novel Acridines

“…Acridine derivatives also are nitrogen-containing heterocyclic compounds. As for the preparation, there are many procedures such as conventional heating in organic solvents [1], microwave irradiation [2], and using heterogeneous catalysts (e.g., Amberlyst-15, DBSA) [3]. The chemistry of acridine ring system is of considerable interest as it is a core structure in various synthetic pharmaceuticals displaying a broad spectrum of biological activities.…”

Synthesis and antimicrobial activities of novel bisacridine-1,8-dione derivatives

“…In addition, synthesis of only very few bisacridine-1,8-dione derivatives reported in the literature for microwaveheating synthesis in solid phase (Hua et al, 2005). Each of these methods have their own advantages but also suffer from one or more disadvantages such as long reaction time, complex processes, low yield, and hazardous reaction conditions.…”