Ultrasound assisted multicomponent reactions: A green method for the synthesis of N-substituted 1,8-dioxo-decahydroacridines using β-cyclodextrin as a supramolecular reusable catalyst in water

• Published in: Chinese journal of catalysis 2016-01, Vol.37 (1), p.146-152
• Main Authors: Chate, Asha V., Rathod, Umesh B., Kshirsagar, Jagdish S., Gaikwad, Pradip A., Mane, Kishor D., Mahajan, Pravin S., Nikam, Mukesh D., Gill, Charansingh H.
• Format: Article
• Language: English
• Subjects: Biodegradability; Catalysts; Derivatives; Michael reaction; N-Substituted 1,8-dioxo-decahydroacridines; Reusable; Supramolecular catalysis; Synthesis; Tandem reaction; Transformations; Ultrasound; Water; β-Cyclodextrin
• ISSN: 1872-2067; 0253-9837; 1872-2067
• DOI: 10.1016/S1872-2067(15)61005-1

We demonstrate a superficial method for the synthesis of N-substituted 1,8-dioxo-decahydroacridines using β-cyclodextrin as a supramolecular, biodegradable, and reusable catalyst in aqueous medium. The reaction product is in excellent yield with moderate to excellent selectivity. The mechanistic transformation presumably proceeds via a one-pot, multicomponent cyclization of dimedone in the presence of aromatic aldehydes and aromatic amines/INH, undergoing a tandem Michael addition reaction. The proposed approach in this study provides a highly efficient and environmentally benign route to N-substituted 1,8-dioxo-decahydroacridines. A mild and environmentally benign protocol was developed using β-cyclodextrins as a catalyst to significantly improve the yield of N-substituted 1,8-dioxo-decahydroacridine derivatives. The β-cyclodextrin employed in the multi-component reaction satisfies the requirements for green chemistry.