Iodine-Catalyzed Mild and Efficient Method for the Synthesis of Chalcones

Sashidhara, Koneni V.; Rosaiah, Jammikuntla N.; Kumar, Abdhesh

doi:10.1080/00397910802654724

Cited by 25 publications

(15 citation statements)

References 33 publications

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“…In the present study, iodine was investigated as a catalyst for the reaction of alcohols with nitriles. Recently, iodine has been investigated as a potential efficient catalyst in several organic reactions because it has low toxicity [6][7][8][9][10][11][12][13][14][15][16][17][18] . In this study, we also investigated solvent-free conditions, from the viewpoint of green chemistry .…”

Section: Introductionmentioning

confidence: 99%

Amidation of Alcohols with Nitriles under Solvent-free Conditions Using Molecular Iodine as a Catalyst

et al. 2010

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Section: Introductionmentioning

confidence: 99%

Amidation of Alcohols with Nitriles under Solvent-free Conditions Using Molecular Iodine as a Catalyst

et al. 2010

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“…In the first route, methylation of 2-hydroxy-4-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde (1) at the 2-position to form the protected aldehyde 2 followed by Claisen-Schmidt condensation 11 with 4-hydroxyacetophenone (3) gave the chalcone prenyl ether (4). This underwent a [3,3]-sigmatropic rearrangement with acetic anhydride in N,N-diethylaniline to give the acety- In the third route, treatment of 2-chloro-4-methoxyacetophenone with tosylmethyl isocyanide (TOSMIC) gave a nitrile compound that was methylated and subjected to an S N 2 reaction followed by a series of functional-group transformations to give the required prenylated benzaldehyde, which was converted into licochalcone A (Scheme 3).…”

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confidence: 99%

Concise Synthesis of Licochalcone A through Water-Accelerated [3,3]-Sigmatropic Rearrangement of an Aryl Prenyl Ether

Jeon¹,

Kim²,

Jun³

2010

Synthesis

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Claisen-Schmidt condensation of 4-(tetrahydropyran-2-yloxy)acetophenone with 2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde gave a THP-protected chalcone ether. Removal of the THP group under mild acidic conditions gave the corresponding chalcone ether, which underwent a water-accelerated Claisen rearrangement under microwave irradiation or heating in a sealed tube in aqueous ethanol to give a good yield of licochalcone A, which has diverse biological activities; no product of deprenylation or abnormal Claisen rearrangement was formed. The abnormal Claisen rearrangement of g-substituted allyl aryl ethers is known to be a problem in [3,3]-sigmatropic rearrangement reaction; this, however, was not detected in our water-accelerated system.

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“…Therefore, in this study, we investigated the synthesis of cinnamyl ethers from α-vinylbenzyl alcohol in one step without the isolation of cinnamyl alcohol using iodine as a catalyst. Iodine is easy to handle and has low toxicity, and it has been found to be an efficient catalyst in several organic reactions [6][7][8][9][10][11][12][13][14][15][16] . We previously reported iodine to be an effi cient catalyst in the intramolecular etherifi cation of 1,3-diols 17 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Cinnamyl Ethers from .ALPHA.-Vinylbenzyl Alcohol Using Iodine as Catalyst

et al. 2010

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Reactions of α-vinylbenzyl alcohol with other alcohols using iodine as a catalyst were investigated. The corresponding cinnamyl ethers were obtained as products. This suggested that α-vinylbenzyl alcohol was converted to cinnamyl ethers via 1-phenylallyl cation. Cinnamyl ethyl ether was obtained in 75% yield by the reaction of α-vinylbenzyl alcohol and ethanol in acetonitrile with iodine under the following conditions: temperature = 50 °C, molar ratio of α-vinylbenzyl alcohol:ethanol:iodine = 1:3.0:0.2, and time period = 6 h. Generally, the yields of the reactions using primary alcohols were higher than those using secondary and tertiary alcohols. Ether interchange also occurred by the reaction of α-vinylbenzyl alcohol and iodine, but proceeded smoothly only when an allyl group was used as the other substituent of the starting ether.

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Iodine-Catalyzed Mild and Efficient Method for the Synthesis of Chalcones

Cited by 25 publications

References 33 publications

Amidation of Alcohols with Nitriles under Solvent-free Conditions Using Molecular Iodine as a Catalyst

Amidation of Alcohols with Nitriles under Solvent-free Conditions Using Molecular Iodine as a Catalyst

Concise Synthesis of Licochalcone A through Water-Accelerated [3,3]-Sigmatropic Rearrangement of an Aryl Prenyl Ether

Synthesis of Cinnamyl Ethers from .ALPHA.-Vinylbenzyl Alcohol Using Iodine as Catalyst

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