Tetrahydronaphthalene as a precursor of new series of chalcones, flavanones, and flavones

Authors

AHMED MEDDEB
GHALIA BOUHALLEB
JULIEN LEGROS
FARHAT REZGUI

DOI

10.3906/kim-1612-2

Abstract

An efficient synthetic route for a novel series of chalcones 2a-2d as well as for the corresponding flavanones 3a-3d and flavones 4a-4d, using functionalized tetrahydronaphthalene (THN), is described herein. The Claisen-Schmidt condensation of such THN and aromatic aldehydes, in the presence of an aqueous solution of KOH (40%), selectively gives the expected chalcones 2a-2d, which may further undergo an intramolecular oxa-Michael addition using piperidine, affording the corresponding flavanones 3a-3d in high yields. Alternatively, treatment of such chalcones 2a-2d with I$_{2}$/DMSO provides rapidly, in a one-pot oxidative cyclization, a series of flavones 4a-4d in excellent yields ranging from 85% to 90%.

Keywords

Morita-Baylis-Hillman, tetrahydronaphthalene, chalcone, flavanone, flavone

First Page

237

Last Page

246

Recommended Citation

MEDDEB, AHMED; BOUHALLEB, GHALIA; LEGROS, JULIEN; and REZGUI, FARHAT (2018) "Tetrahydronaphthalene as a precursor of new series of chalcones, flavanones, and flavones," Turkish Journal of Chemistry: Vol. 42: No. 2, Article 3. https://doi.org/10.3906/kim-1612-2
Available at: https://journals.tubitak.gov.tr/chem/vol42/iss2/3