• Title/Summary/Keyword: ${\beta}$-Enaminone

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NaHSO4/SiO2: An Efficient Catalyst for the Synthesis of β-Enaminones and 2-Methylquinolin-4(1H)-Ones under Solvent-Free Condition (NaHSO4/SiO2: Solvent-Free 반응 조건에서 β-Enaminone들과 2-Methylquinolin-4(1H)-One들의 합성을 위한 효율적인 촉매)

  • Sapkal, Suryakant B.;Shelke, Kiran F.;Shingate, Bapurao B.;Shingare, Murlidhar S.
    • Journal of the Korean Chemical Society
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    • v.54 no.6
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    • pp.723-726
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    • 2010
  • An efficient and simplified protocol for $NaHSO_4/SiO_2$ catalyzed solvent-free synthesis of $\beta$-enaminone and 2-methylquinolin-4(1H)-one derivatives under microwave irradiation is described. A series of functionalized derivatives have been synthesized in shorter reaction times with moderate to good yields. The use of milder catalyst in non-conventional method offers significant advantages over conventional methods, such as higher selectivities, simplicity, solvent-free reaction and non-environmental polluting conditions.

Efficient One-Pot Synthesis of Acridinediones by Indium(III) Triflate-Catalyzed Reactions of β-Enaminones, Aldehydes, and Cyclic 1,3-Dicarbonyls

  • To, Quang Huy;Lee, Yong-Rok;Kim, Sung-Hong
    • Bulletin of the Korean Chemical Society
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    • v.33 no.4
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    • pp.1170-1176
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    • 2012
  • An efficient one-pot synthesis of acridinediones by $In(OTf)_3$-catalyzed reactions was developed starting from ${\beta}$-enaminones, aldehydes, and cyclic 1,3-diketones. The key strategies of these reactions involve domino Knoevenagel condensation/Michael addition/cyclodehydration reaction.

A Kinetic Study on Michael-type Reactions of 1-(X-Substituted Phenyl)-2-propyn-1-ones with Amines: Effect of Amine Nature on Reactivity and Mechanism

  • Um, Ik-Hwan;Hwang, So-Jeong;Lee, Eun-Ju
    • Bulletin of the Korean Chemical Society
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    • v.29 no.4
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    • pp.767-771
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    • 2008
  • Second-order rate constants have been measured spectrophotometrically for the Michael-type reaction of 1-(Xsubstituted phenyl)-2-propyn-1-ones (2a-f) with amines in $H_2O$ at 25.0 ${\pm}$ 0.1 ${^{\circ}C}$. A linear Brønsted-type plot is obtained with ${\beta}_{nuc}$ = 0.25 ${\pm}$ 0.02, a typical $\beta_{nuc}$ value for reactions which proceed through a stepwise mechanism with attack of amine on the electrophilic center being the rate-determining step. Secondary alicyclic amines are found to be more reactive than isobasic primary amines. The Hammett plot for the reactions of 2a-f with morpholine is not linear, i.e., the substrate with a strong electron-donating group (e.g., 4-MeO) exhibits a negative deviation from the Hammett plot. However, the Yukawa-Tsuno plot for the same reactions exhibits an excellent linear correlation with ρ = 0.62 and r = 0.82. Thus, it has been proposed that the nonlinear Hammett plot is not due to a change in the ra te-determining step but due to ground-state stabilization through resonance interactions.