An Interesting Synthetic Pathway to Some Quinolin-4(1H)ones: Phenacylanthranilates Rearrangement – Limits and Scopes

Author(s): Miroslav Soural, Pavel Hradil, Sona Krupkova, Jan Hlavac.

Journal Name: Mini-Reviews in Organic Chemistry

Volume 9 , Issue 4 , 2012

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Abstract:

Rearrangement of some anthranilic acid esters, thioesters or amides under particularly acidic conditions gives derivatives of 2- aryl-3-substituted-quinolinon-4(1H)-ones. The reaction represents undoubtely the most efficient method for the preparation of derivatives bearing hydroxy and amino group at position 3. Furthermore, the target compounds comprise organic molecules with very interesting biological properties that have been reviewed quite recently. This mini-review summarizes information about limits and scopes of the unprecedent reaction that became extremely useful and revolutionary in area of flavonoids analogues research.

Keywords: Rearrangement, cyclization, aminoquinolinones, hydroxyquinolinones, anthranilic acids, haloketones.

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Article Details

VOLUME: 9
ISSUE: 4
Year: 2012
Page: [426 - 432]
Pages: 7
DOI: 10.2174/157019312804699483
Price: $65

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