Facile and Highly Efficient Procedure for the Synthesis of Triazolyl Methoxyphenyl 1,8-Dioxo-decahydroacridines via One-Pot, Pseudo-Five-Component Reaction

Abstract

A series of triazolyl methoxyphenyl 1,8-dioxo-decahydroacridine derivatives has been prepared in a one-pot, pseudo-five-component reaction of aromatic propargylated aldehydes, various azides, dimedone, and a variety of amines in the presence of Cu(OAc)₂/sodium ascorbate and 1-methylimidazolium trifluoroacetate ([Hmim]TFA) as the catalyst in good yields.

GRAPHICAL ABSTRACT

Keywords:

• Click multicomponent
• decahydroacridine
• one-pot reaction
• pseudo-five-component reaction
• triazole

ACKNOWLEDGMENTS

We gratefully acknowledge financial support from the Research Council of Shahid Beheshti University and the Catalyst Center of Excellence (CCE).

Notes

^a Reaction conditions: propargylated aldehyde 1a (1 mmol), 4-nitrophenyl azide 2a (1 mmol), 3-nitroaniline 3b (1.2 mmol), and dimedone 4 (2 mmol).

^b In all reactions the conditions were optimized for a 100% conversion.

^c The reactions were run in the presence of 10 mol% of catalyst.

^d Isolated yield based on 1a.

^e The reaction was run under neat conditions.

^f Only compound 6 was isolated.

^a Isolated yield.