A Convenient Method for Synthesizing 2-Aryl-3-hydroxy-4-oxo-4<i>H</i>-1-benzopyrans or Flavonols

Fougerousse, André; González, Emmanuel; Brouillard, Raymond

doi:10.1021/jo990735q

Cited by 72 publications

(32 citation statements)

References 19 publications

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“…According to the references, [15][16][17] the reaction of 2 0 -hydroxyacetophenone derivatives with a series of 2-chlorobenzoyl chloride in pyridine provided 2-acetylphenyl 2-chlorobenzoate derivatives 11 in good-to-excellent yields.…”

Section: Resultsmentioning

confidence: 99%

A New Protocol for Total Synthesis of Natural Product Frutinone A and Its Derivatives

Lei¹,

Sun²,

Tao³

et al. 2016

Aust. J. Chem.

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A new protocol for total synthesis of natural product frutinone A was accomplished in three steps by using inexpensive 2 0 -hydroxyacetophenone as starting material. The key intermediate 3-(2-chlorobenzoyl)-4-hydroxycoumarin was synthesized in one pot through Baker-Venkataraman rearrangement of 2-acetylphenyl 2-chlorobenzoate followed by introduction of methyl chloroformate under basic conditions. Then, base-promoted intramolecular nucleophilic substitution reaction of 3-(2-chlorobenzoyl)-4-hydroxycoumarin provided frutinone A in excellent yield. The synthetic route features good yield, transition metal-free and mild reaction conditions, and high tolerance for functionality, thereby allowing easy substitutions around the frutinone A core.

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Section: Resultsmentioning

confidence: 99%

A New Protocol for Total Synthesis of Natural Product Frutinone A and Its Derivatives

Lei¹,

Sun²,

Tao³

et al. 2016

Aust. J. Chem.

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“…[28] The key step in the synthesis of the (E)-3-bromo-2-styryl-4H-chromen-4-ones 3a and 3d-k involves treatment of ketones 11a-i with phenyltrimethylammonium tribromide (PTT) in THF at room temperature. The presence of this reactant promotes a one-pot transformation, involving ketone α-bromination [29] followed by cyclisation to afford, after careful column chromatographic purification, the 3-bromo-2-styryl-4H-chromen-4-ones 3a and 3d-k.…”

Section: Synthesesmentioning

confidence: 99%

“…The obtained methoxylated 2,3-diaryl-9H-xanthen-9-ones were recrystallised from ethanol and obtained in moderate to good yields (Table 3). +· (14), 379 (29), 378 (100), 377 (30) …”

Section: Synthesis Of the Methoxylated 23-diaryl-9h-xanthen-9-ones 5mentioning

confidence: 99%

Efficient Syntheses of New Polyhydroxylated 2,3‐Diaryl‐9H‐xanthen‐9‐ones

2009

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A large number of hydroxylated 2,3-diaryl-9H-xanthen-9-ones have been synthesised by two different approaches, starting either from 3-bromo-2-methyl-4H-chromen-4-one or from (E)-3-bromo-2-styryl-4H-chromen-4-ones. The former method involves Heck reactions between 3-bromo-2-methyl-4H-chromen-4-one and styrenes, leading to (E)-2-methyl-3-styryl-4H-chromen-4-ones; these condensed with benzaldehyde to give (E,E)-2,3-distyryl-4H-chromen-4-ones, which led to the desired 2,3-diaryl-9H-xanthen-9-ones under reflux in 1,2,4-trichlorobenzene. 3-Bromo-2-styryl-4H-chromen-4-ones were obtained either by aldol condensations between 3-bromo-2-methyl-4H-chromen-4-one and benzaldehydes, or through Baker-Venkataraman rearrangements of 2-acetylphenyl cinnamates, followed by one-pot bromination/ cyclisation with phenyltrimethylammonium tribromide. The 2,3-diaryl-9H-xanthene-9-ones were obtained in one-pot transformations involving Heck reactions between (E)-3-

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“…First, the Algar-Flynn-Oyamada reaction based on the oxidative cyclization of 2'-hydroxychalcones should be mentioned since one of the products is aurone. [129][130][131][132][133] Another procedure described by Donnelly et al 134,135 is also based on the reactions of chalcones. 2'-acetoxychalcones are first bromomethylated and the ring closure of the bromodihydro-chalcones provides aurones.…”

Section: Synthesis Of Auronesmentioning

confidence: 99%

Synthesis of exocyclic α,β-unsaturated ketones

Lévai

2003

Arkivoc

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This review describes synthetic procedures for the preparation of selected groups of the most important exocyclic α,β-unsaturated ketones. Some of these α,β-enones, víz. aurones and 3-benzylidene-4-chromanones belong to the natural products. The others are synthetic substances which are convenient and especially important intermediates for the stereoselective synthesis of polycyclic ring systems. To illustrate the utility of any special procedures, relevant examples have been included. However, it is not the aim of the present review article to list and evaluate all the papers published in this field. Owing to the huge number of papers, such a goal would be an almost unrealizable task.

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A Convenient Method for Synthesizing 2-Aryl-3-hydroxy-4-oxo-4H-1-benzopyrans or Flavonols

Cited by 72 publications

References 19 publications

A New Protocol for Total Synthesis of Natural Product Frutinone A and Its Derivatives

A New Protocol for Total Synthesis of Natural Product Frutinone A and Its Derivatives

Efficient Syntheses of New Polyhydroxylated 2,3‐Diaryl‐9H‐xanthen‐9‐ones

Synthesis of exocyclic α,β-unsaturated ketones

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