• Title/Summary/Keyword: Cyclodehydration

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New and General Methods for the Synthesis of Arylmethylene Bis(3-Hydroxy-2-Cyclohexene-1-Ones) and Xanthenediones by EDDA and In(OTf)3-Catalyzed One-Pot Domino Knoevenagel/Michael or Koevenagel/Michael/Cyclodehydration Reactions

  • Jung, Doo-Hwan;Lee, Yong-Rok;Kim, Sung-Hong;Lyoo, Won-Seok
    • Bulletin of the Korean Chemical Society
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    • v.30 no.9
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    • pp.1989-1995
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    • 2009
  • Efficient one-pot synthesis of arylmethylene bis(3-hydroxy-2-cyclohexene-1-ones) and xanthenediones by EDDA and In($OTf)_3$-catalyzed reactions was developed starting from dimedone and aryl aldehydes. The key strategies of these reactions involve domino Knoevenagel/Michael reaction or Koevenagel/Michael/Cyclodehydration reactions. The scope and limitation of the two catalysts under various reaction conditions were investigated and described.

Studies on the Styrenic Polymers(1), Imidization of Poly(styrene-co-maleic anhydrides) and Their Thermal Properties (Styrenic Polymers연구(1), Poly(styrene-co-maleic anhydride)의 이미드화와 열적 성질)

  • Ahn, Tae-Oan;Park, Lee-Soon;Lee, Sang-Soo;Kim, Gi-Heon
    • Applied Chemistry for Engineering
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    • v.3 no.1
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    • pp.179-187
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    • 1992
  • Poly(styrene-co-maliec anhydride) was reacted with aromatic amines such as aniline, p-toluidine, and p-chloroaniline in 10% (w/w) DMF solution to convert maleic anhydride units into maleimides. Optimum reaction conditions for cyclodehydration step of imide ring formation were : (a) reaction temp. of $80^{\circ}C$ (b) mole ratios of cyclodehydration agents : anhydride units in SMA/acetic anhydride/sodium acetate/triethyl amine= 1.0/2.0/0.2/1.1. $T_g$of SMI(imide modified SMA) was increased with increasing degree of imidization, but $T_g$leveled off in the early stage of imide content. And $T_g$of SMI was increased with the following order of amines used for imidization reagents : aniline < p-toluidine < p-chloroaniline.

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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.

Synthesis of Higenamine, A Cardiotonic Principle of Aconite Root

  • Chang, Ki-Churl;Choi, Sook-Yun;Lim, Jung-Kyoo;Park, Chan-Woong
    • Archives of Pharmacal Research
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    • v.7 no.2
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    • pp.133-136
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    • 1984
  • Higenamine (I), cardiotonic principle of Aconite root, was synthesized from 4-methoxy-phenylacetic acid (II) and .betha.-(3, 4-dimethoxyphenyl)-ethylamine (IV). Condensation of IV with 4-mehoxyphenylacetyl chloride (III) was followed by cyclodehydration yielding 1-(4'-methoxybenzyl)-6, 7- dimethoxy-3, 4-dihydroisoquinoline (VI). Reduction of VI to 1, 2, 3, 4-tetrahydroisoquinoline (VII) and subsequent demethylation provided desired product higenamine, 1-(4'-hydroxybenzyl)-6, 7- dihydroxy-1, 2, 3, 4, -tetrahydroisoquinoline.

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Expeditious Synthesis of Natural Benzofuran, Eupomatenoid-6 by Umpolung of α-Aminophosphonates

  • Damodar, Kongara;Jun, Jong-Gab
    • Bulletin of the Korean Chemical Society
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    • v.35 no.12
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    • pp.3618-3622
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    • 2014
  • Simple and practical synthesis of natural benzofuran derivative eupomatenoid-6 via Horner-Emmons type condensation as the key step is described. The umpolung property of aldehyde derivative, ${\alpha}$-aminophosphonate was efficiently employed in this reaction. ${\alpha}$-Aminophosphonate of anisaldehyde subjected to Horner-Emmons type condensation with 5-bromo-2-methoxybenzaldehyde to yield the deoxybenzoin, which was further methylated and then underwent tandem demethylation-cyclodehydration to afford the benzofuran scaffold in excellent yield. Finally Suzuki coupling with propenyl boronic acid afforded eupomatenoid-6 with an overall yield of 56.8%.