2004
DOI: 10.1016/j.tetlet.2004.08.044
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Iodine-catalyzed synthesis of β-keto enol ethers

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Cited by 56 publications
(25 citation statements)
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“…See [18] [19]. As displayed in the Scheme, the dione D could be converted into the compound 7 through a surfacemediated Michael addition with methyl vinyl ketone (MVK), supported on activated neutral Al 2 O 3 , without any solvent, and further treatment with I 2 and MeOH according to the following procedure.…”
Section: Experimental Partmentioning
confidence: 99%
“…See [18] [19]. As displayed in the Scheme, the dione D could be converted into the compound 7 through a surfacemediated Michael addition with methyl vinyl ketone (MVK), supported on activated neutral Al 2 O 3 , without any solvent, and further treatment with I 2 and MeOH according to the following procedure.…”
Section: Experimental Partmentioning
confidence: 99%
“…Molecular iodine [28][29][30][31] has attracted attention as an inexpensive, non toxic, readily available catalyst for various organic transformations to afford the corresponding products in excellent yields with high selectivity. It has been used as a mild Lewis acid in the dehydration of tertiary alcohols to alkenes, in the formation of ethers, as well as β-keto enol ethers, [32][33][34] for esterification, 35 transesterification, 36 acetylation 29 and benzothiophene 37 formation, but there are only a few reports about its use for the synthesis of 1,4-DHPs. 38,39 Therefore, we decided to synthesize some new symmetrical, unsymmetrical and N-substituted 1,4-DHPs promoted by a catalytic amount of iodine under ambient conditions with good to excellent yields.…”
Section: Introductionmentioning
confidence: 99%
“…Iodine-catalyzed and -mediated syntheses of benzyl alkyl ethers, 19 benzothiophenes, 20 bis-indols, 21 β-keto enol ethers, 22 chalcones, 23 quinolines, 24 and isoquinolines 25 were already reported. However, iodine-catalyzed formal [3+3] cycloadditon of 1,3-carbonyls to α,β-unsaturated aldehydes to afford 2H-pyrans has not been examined.…”
mentioning
confidence: 99%