Synthesis of 2-(4-amino substituted benzylidene) indanone analogues from aromatic nucleophilic substitution (S_NAr) reaction

Abstract

A novel, efficient and convenient procedure has been developed for the synthesis of 2-(4-amino-substituted benzylidene)indanone derivatives. In the first step, the reaction of 4-fluorobenzaldehyde with 5, 6-dimethoxy-2, 3-dihydro-1H-inden-1-one in the presence of NaOH in EtOH was described. In the next step, a variety of aliphatic and aromatic amines were reacted with 2-(4-fluorobenzylidene)-5, 6-dimethoxy-2, 3-dihydro-1H-Inden-1-one via aromatic substitution (S_NAr) reaction to produce 2-(4-aminobenzylidene)-5, 6-dimethoxy-2, 3-dihydro-1H-Inden-1-one derivatives as a novel class of 1-indanones. These products have been successfully prepared in good to excellent yields. ¹H and ¹³C NMR, FT-IR spectroscopy and CHN analysis supported the proposed structures of the products.

Graphical Abstract

Keywords:

• Alzheimer’s disease
• donepezil
• indanone
• nucleophilic aromatic substitution (SNAr)

Additional information

Funding

We thank the Research Affairs of the University of Tabriz for financial support.