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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 17
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Research Paper

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

, , &
Pages 2253-2259 | Received 19 May 2018, Published online: 07 Aug 2018
 

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 (SNAr) 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. 1 H and 13 C NMR, FT-IR spectroscopy and CHN analysis supported the proposed structures of the products.

Graphical Abstract

Additional information

Funding

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

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