A New and Efficient Synthesis of 3-Halogenated 4<i>H</i>-1-Benzopyran-4-ones

Gammill, Ronald B.

doi:10.1055/s-1979-28869

Cited by 90 publications

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“…The following compounds were prepared following the procedure described in the literature: iodophenols 8 13 and 12 14 ; 3-iodo- N -tosylindole ( 49 ), 15 3-iodo-4 H -chromen-4-one ( 51 ), 16 2-iodo-4,4-dimethylcyclohexenone ( 63 ). 17 …”

Section: Methodsmentioning

confidence: 99%

Efficient microwave-assisted one-pot three-component synthesis of 2,3-disubstituted benzofurans under Sonogashira conditions

2013

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An efficient one-pot method for the synthesis of 2,3-disubstituted benzo[b]furans from commercially available 2-iodophenols, terminal acetylenes and aryl iodides has been developed utilizing Sonogashira reaction conditions. After an initial Sonogashira coupling of the 2-iodophenol with the terminal alkyne, cyclization involving the aryl iodide provides the 2,3-disubstituted benzo[b]furan in good to excellent yields. The use of microwave irradiation shortens the reaction times and minimizes the side products. This methodology is especially useful for the construction of libraries of highly substituted benzo[b]furans and their analogues.

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Section: Methodsmentioning

confidence: 99%

Efficient microwave-assisted one-pot three-component synthesis of 2,3-disubstituted benzofurans under Sonogashira conditions

2013

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“…ether cleavage provided the corresponding isoflavones 11,13,15,17,19,21,23,25,27,29,31,33,35,37,39,41,43,45,47 and 49 (Scheme 2 B). [16] O-Methylation of 7-hydroxy-benzopyran-4-one derivatives 13, 19, 25 and 33 with methyl iodide provided compounds 50-53 (Scheme 3 A).…”

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confidence: 99%

Identification of Benzopyran‐4‐one Derivatives (Isoflavones) as Positive Modulators of GABA_A Receptors

et al. 2011

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Isoflavones do it too! Enhancement of chloride ion flux at GABAA receptors by positive modulators is an important therapeutic strategy for the treatment of central nervous system (CNS)‐related disorders. Benzopyran‐4‐one derivatives (isoflavones), identified by systematic structure‐driven design, exhibit potent flumazenil‐insensitive positive modulation at human recombinant α1β2γ2L receptors expressed in Xenopus oocytes.

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“…The residual solid was purified by column chromatography on silica gel (35 g, CHCl 3 ) to give enamine 11 (2. 10 3-Iodo-6,7-dimethoxy-4H-chromen-4-one (3). To a stirred solution of enamine 11 (1.07 g, 4.53 mmol) in CHCl 3 (22 mL) were added pyridine (650¯L, 8.12 mmol) and I 2 (2.47 g, 9.73 mmol) at 0°C.…”

Section: Methodsmentioning

confidence: 99%

Practical Synthesis of Glaziovianin A, a Cytotoxic Isoflavone, and Its O7-Propargyl Analogue

Hayakawa¹,

Shioda

Ikedo

et al. 2014

Bulletin of the Chemical Society of Japan

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A New and Efficient Synthesis of 3-Halogenated 4H-1-Benzopyran-4-ones

Cited by 90 publications

References 0 publications

Efficient microwave-assisted one-pot three-component synthesis of 2,3-disubstituted benzofurans under Sonogashira conditions

Efficient microwave-assisted one-pot three-component synthesis of 2,3-disubstituted benzofurans under Sonogashira conditions

Identification of Benzopyran‐4‐one Derivatives (Isoflavones) as Positive Modulators of GABA_A Receptors

Practical Synthesis of Glaziovianin A, a Cytotoxic Isoflavone, and Its O7-Propargyl Analogue

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A New and Efficient Synthesis of 3-Halogenated 4H-1-Benzopyran-4-ones

Cited by 90 publications

References 0 publications

Efficient microwave-assisted one-pot three-component synthesis of 2,3-disubstituted benzofurans under Sonogashira conditions

Efficient microwave-assisted one-pot three-component synthesis of 2,3-disubstituted benzofurans under Sonogashira conditions

Identification of Benzopyran‐4‐one Derivatives (Isoflavones) as Positive Modulators of GABAA Receptors

Practical Synthesis of Glaziovianin A, a Cytotoxic Isoflavone, and Its O7-Propargyl Analogue

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Identification of Benzopyran‐4‐one Derivatives (Isoflavones) as Positive Modulators of GABA_A Receptors