Synthesis of Some Bromo‐Substituted 3‐Aroyl Flavanones and Flavones

Mahalle, Prashant R.; Khaty, Niraj T.

doi:10.1155/2010/158274

Cited by 6 publications

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“…Numerous methods have been developed for flavones synthesis, including Baker-Venkataraman rearrangement, 21,22 the Allan-Robinson protocol, 23 and the reaction of oxidative cyclization of chalcones using numerous oxidizing agents such as DDQ, 24 Ph-S-S-Ph, 25,26 In our previous reports on the chemistry of Morita-Baylis-Hillman, we described the synthesis of a series of functionalized THN, 32 and currently we are interested in their further synthetic applications. In this paper, we wish to report our results dealing with the conversion of theses derivatives into new chalcones that may further undergo an intramolecular oxa-Michael addition, yielding the corresponding flavanones.…”

Section: Introductionmentioning

confidence: 99%

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

Meddeb¹,

Bouhalleb²,

Legros³

et al. 2018

Turk J Chem

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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 ClaisenSchmidt 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%.

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