Synthesis and Structural Features of Indanone, Tetralone and Naphthone Derivatives: Selective Fluorination and Condensation Products

The present study aims to investigate the synthesis and structural features of Indanone, Tetralone and Naphthone derivatives. Indanone, tetralone and naphthone derivatives and fused-ring heterocycles have been prepared via Claisen condensations, arylhydrazine condensations, Baker-Venkataraman rearrangements, Claisen-Schmidt reactions, selective fluorinations and trifluoroacetylations in yields ranging from 22-92%. Of particular interest is the regiochemistry and stereochemistry observed in these products and their utility as scaffolds for the preparation of heterocyclic derivatives. We also note unusual transformations including a novel one-pot, dual trifluoroacetylation, trifluoroacetylnaphthone synthesis via a deacetylation as well as an acetyl-trifluoroacetyl group exchange. Solid-state structural features exhibited by these compounds were investigated using crystallographic methods. Moreover, Selective incorporation of fluorine and fluorine-containing groups into these heterocyclic products will be a focus of this work. We anticipate reporting these findings in the near future.