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

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

November 4, 2020 Chemical Science 0


The present study seeks to investigate the synthesis and structural characteristics of derivatives of Indanone, Tetralone and Naphthone. Via Claisen condensations, arylhydrazine condensations, BakerVenkataraman rearrangements, Claisen-Schmidt reactions, selective fluorinations and trifluoroacetylations in yields ranging from 22-92 percent, indanone, tetralone and naphthone derivatives and fused-ring heterocycles were prepared. Regiochemistry and stereochemistry observed in these products and their usefulness as scaffolds for the preparation of heterocyclic derivatives are of particular interest. Unusual changes such as a novel one-pot, dual trifluoroacetylation, trifluoroacetylnaphthone synthesis via deacetylation and an exchange of the acetyltrifluoroacetyl group are also noted. Using crystallographic methods, solid-state structural features exhibited by these compounds were investigated. In addition , this study will concentrate on the selective introduction of fluorine and fluorine-containing groups into these heterocyclic materials. In the near future , we expect these results to be announced.

Author(s) Details

Paul D. Boyle
Department of Chemistry, Western University, 1151 Richmond St., London, Ontario, N6A 5B7, Canada.

David Breaud
School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, GA 30043, USA.

Matthew Churley
School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, GA 30043, USA.

Patrick Coppock, Jr.
School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, GA 30043, USA.

Elvia Encarnacion-Thomas
School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, GA 30043, USA.

Chloe Fernandes
School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, GA 30043, USA.

Augustus W. Fountain
Department of Chemistry and Biochemistry, University of South Carolina, 631 Sumter Street Columbia, SC 29208, USA.

Cristina Gomez
Department of Chemistry and Life Science, United States Military Academy, 646 Swift Road, West Point, NY 10996, USA.

Alejandro Guzman
School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, GA 30043, USA.

James L. Jackson
US Army Corps of Engineers, 101 West Oglethorpe Avenue, Savannah, GA 31401, USA.

Linh Lam
School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, GA 30043, USA.

Ajay Mallia
School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, GA 30043, USA.

Samantha Moseley
School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, GA 30043, USA.

Sang H. Park
School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, GA 30043, USA.

William F. Pearman
Department of Chemistry and Life Science, United States Military Academy, 646 Swift Road, West Point, NY 10996, USA.

Robert D. Schmidt
Department of Chemistry, North Carolina State University, P.O. Box 8204, Raleigh, NC 27695, USA.

Joseph C. Sloop
School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, GA 30043, USA.

Roger D. Sommer
Molecular Education, Technology, and Research Innovation Center, North Carolina State University, 2620 Yarbrough Dr., Raleigh, NC 27695, USA.

Stephanie Stalker
School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, GA 30043, USA.

Jonathan Weyand
Department of Chemistry and Life Science, United States Military Academy, 646 Swift Road, West Point, NY 10996, USA.

Karla Wilmott
School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, GA 30043, USA.

Jonathan Yi
School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, GA 30043, USA.

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