Studies on the C-Methyl-γ-benzopyrone System. Orientation in the Isoflavone Series. II<sup>1</sup>

Rahman, W.; Nasim, Kh. Takrimullah

doi:10.1021/jo01059a021

Cited by 10 publications

(1 citation statement)

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“…The Baker-Venkataraman rearrangement has also been used as a key step in the synthesis of trihydroxyflavanones 51 47 as well as isoflavones 54 48 (Scheme 11).…”

Section: Syn Thesismentioning

confidence: 99%

Mechanism and Application of Baker–Venkataraman O→C Acyl Migration Reactions

Ameen

Snape

2014

Synthesis

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This literature review focuses on the O→C acyl migration of aryl esters to yield the corresponding 1,3-dicarbonyl products-a reaction known as the Baker-Venkataraman rearrangement-and outlines their subsequent transformations. The purpose of the review is to highlight the utility of the rearrangement which provides a key step in the synthesis of various heterocyclic motifs. The scope of the BakerVenkataraman rearrangement is illustrated by way of numerous examples of its application, and in doing so, the review contains over 100 references and covers just over 100 years of the literature, from the first report of the rearrangement by Auwers in 1910 up to more recent examples in the past few years.

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“…The Baker-Venkataraman rearrangement has also been used as a key step in the synthesis of trihydroxyflavanones 51 47 as well as isoflavones 54 48 (Scheme 11).…”

Section: Syn Thesismentioning

confidence: 99%

Mechanism and Application of Baker–Venkataraman O→C Acyl Migration Reactions

Ameen

Snape

2014

Synthesis

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Allan‐Robinson Condensation

2010

Comprehensive Organic Name Reactions and Reagents

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It has been found that flavones or isoflavones derivatives are synthesized by means of the condensation between o ‐hydroxyaryl ketones and an anhydride of aromatic acid in the presence of the sodium salt of corresponding acid in the anhydride. This reaction is known as the Allan‐Robinson condensation. This reaction has wide application in formation of organic synthesis. The structurally disparate flavonoids and isoflavones have been synthesized using this method.

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Baker‐Venkataraman Rearrangement

2010

Comprehensive Organic Name Reactions and Reagents

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The rearrangement of o ‐acyloxyketones into β‐diketones under basic conditions is generally referred to as the Baker–Venkataraman rearrangement or Baker–Venkataraman transformation. This intramolecular acyl transfer reaction has become a major reaction in flavone chemistry and the migration of acyl group has been confined to aromatic or heteroaromatic acyl group. The resulting molecules from this reaction have been applied to the synthesis of chromones and flavones.

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Studies on the C-Methyl-γ-benzopyrone System. Orientation in the Isoflavone Series. II¹

Cited by 10 publications

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Mechanism and Application of Baker–Venkataraman O→C Acyl Migration Reactions

Mechanism and Application of Baker–Venkataraman O→C Acyl Migration Reactions

Allan‐Robinson Condensation

Baker‐Venkataraman Rearrangement

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Studies on the C-Methyl-γ-benzopyrone System. Orientation in the Isoflavone Series. II1

Cited by 10 publications

References 0 publications

Mechanism and Application of Baker–Venkataraman O→C Acyl Migration Reactions

Mechanism and Application of Baker–Venkataraman O→C Acyl Migration Reactions

Allan‐Robinson Condensation

Baker‐Venkataraman Rearrangement

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Product

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Studies on the C-Methyl-γ-benzopyrone System. Orientation in the Isoflavone Series. II¹