Different behaviour of 2-propionyl-4-methyl-6-acetyl-phenol in the kostanecki-robinson acylation and in the baker-venkataraman rearrangement

Re, P. Da; Cimatoribus, Luigi

doi:10.1007/bf02138256

Cited by 9 publications

(1 citation statement)

References 2 publications

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“…The focus of the present study is the synthesis of 2,3,6,8-tetrasubstituted chromones (Figure ). A literature search revealed that only a few chromone derivatives with this substitution pattern have been reported previously. − In addition, the published compounds were cyclized to the chromone after the substituents had been introduced, and only undemanding substituents (e.g. Me, COCH 3 and OH) had been used.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2,3,6,8-Tetrasubstituted Chromone Scaffolds

et al. 2006

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A useful and efficient synthetic strategy to 2,3,6,8-tetrasubstituted chromone derivatives has been developed. 2-Aryl/styryl-8-bromo-6-chloro-3-hydroxychromone derivatives were synthesized and used as scaffolds by introducing a variety of substituents in the 3-, 6-, and 8-positions using palladium-mediated reactions. Excellent regioselectivity in all positions could be obtained by performing reactions in the 8-position first, in which Stille, Heck, Suzuki, and Sonogashira reactions gave good to excellent yields of product (63-98%). Stille and Heck reactions in the 6-position also gave the desired products in good yields (64-86%). The hydroxy group in the 3-position was activated as a triflate and used in productive Stille reactions (63-94%). This hydroxyl group was also used in O-alkylation reactions with different functionalized alkyl bromides (57-88%). The flavonoids, which are based on the chromone structure, and other related ring systems, have several interesting biological activities. The chromones are also interesting structural scaffolds, and they have for example been designed to be used as mimetics of short peptides. The versatile applicability of chromone derivatives and especially their potential use in drug discovery implicates the importance of access to efficient synthetic routes to such compounds.

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Section: Introductionmentioning

confidence: 99%

Synthesis of 2,3,6,8-Tetrasubstituted Chromone Scaffolds

et al. 2006

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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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Kostanecki‐Robinson Reaction

2010

Comprehensive Organic Name Reactions and Reagents

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The formation of coumarins and chromones from alkyl o ‐hydroxyaryl ketone and aliphatic acid anhydride in the presence of the corresponding aliphatic acid sodium salt, via the O ‐acylation and aldol condensation is generally known as the Kostanecki–Robinson reaction. It has been reported that depending on the actual reaction conditions and substituents, either coumarin or chromone or both can be produced. The existing α‐pyrone ring on the aromatic ketone does not affect the reaction.

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Different behaviour of 2-propionyl-4-methyl-6-acetyl-phenol in the kostanecki-robinson acylation and in the baker-venkataraman rearrangement

Cited by 9 publications

References 2 publications

Synthesis of 2,3,6,8-Tetrasubstituted Chromone Scaffolds

Synthesis of 2,3,6,8-Tetrasubstituted Chromone Scaffolds

Baker‐Venkataraman Rearrangement

Kostanecki‐Robinson Reaction

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