• Title/Summary/Keyword: Horner-Wadsworth-Emmons reaction

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A New Synthesis of Triphenylphosphorane Ylide Precursors to α-Keto Amide/Ester and Tricarbonyl Units via Horner-Wadsworth-Emmons Reaction

  • Lee, Kie-Seung
    • Bulletin of the Korean Chemical Society
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    • v.31 no.10
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    • pp.2776-2782
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    • 2010
  • Newly developed Horner-Wadsworth-Emmons (HWE) reagents 5 having triphenylphosphorane ylide subunits readily condensed with various carbonyl compounds under mild reaction conditions to afford $\beta,\gamma$-unsaturated $\alpha$-keto triphenylphorane ylides in good to excellent yields, which were hydrogenated over Pd-C (10%)/$H_2$ (1 atm) to give the corresponding $\alpha$-keto triphenylphorane ylides in quasi-quantitative yields. These triphenyphosphorane ylides have been utilized as the precursors to $\alpha$-keto amide/ester and vicinal tricarbonyl units in Wasserman's synthetic protocols, and have previously been prepared only from carboxylic acids/acid chlorides. Our new approaches provide excellent alternatives for the synthesis of triphenylphosphorane ylide precursors to $\alpha$-keto amide/ester and vicinal tricarbonyl units directly from carbonyl compounds in good to excellent yields.

A Convenient Synthesis of an Anti-Helicobacter Pylori Agent, Dehydrodiconiferyl Alcohol

  • Hu, Kun;Jeong, Jin-Hyun
    • Archives of Pharmacal Research
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    • v.29 no.7
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    • pp.563-565
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    • 2006
  • Potential anti-Helicobacter pylori agent dehydrodiconiferyl alcohol was synthesized in 44% overall yield, starting from vanillin which could be commercially available. Carbon extension of vanillin followed by the Horner-Wadsworth-Emmons reaction, a biomolecular radical coupling reaction and DIBAL-H reduction gave dehydrodiconiferyl alcohol.

Highly Efficient Blue-Light-Emitting Diodes Based on Styrylamine Derivatives End-capped with a Diphenylvinyl Group

  • Kim, Seul-Ong;Lee, Kum-Hee;Kang, Sun-Woo;Lee, Jin-Yong;Seo, Ji-Hoon;Kim, Young-Kwan;Yoon, Seung-Soo
    • Bulletin of the Korean Chemical Society
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    • v.31 no.2
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    • pp.389-396
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    • 2010
  • In this paper, we reported the synthesis and electroluminescent properties of blue fluorescent styrylamine derivatives end-capped with a diphenylvinyl group. A new series of styrylamine derivatives have been synthesized via the Horner-Wadsworth-Emmons reaction. To explore electroluminescent properties of these molecules, multilayer organic lighte-mitting devices with the configuration of ITO/NPB/1-5 doped in MADN/Bphen/Liq/Al were fabricated. All devices exhibited blue emissions with good EL performances. Among those reported herein, the device using dopant 5 exhibited a maximum luminance of $24,000\;cd/m^2$ at 11.0 V, a luminous efficiency of 12.5 cd/A at $20\;mA/cm^2$, a power efficiency of 6.50 lm/W at $20\;mA/cm^2$, and $CIE_{x,y}$ coordinates of (x = 0.173, y = 0.306) at 8.0 V, all of which demonstrate the superiority of these materials in blue OLEDs.

Synthsis and Antiviral Evaluation of Novel 3'-and 4 -Doubly Branched Carbocyclic Nucleosides as Potential Antiviral Agents

  • Hong, Joon-Hee
    • Archives of Pharmacal Research
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    • v.26 no.12
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    • pp.1109-1116
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    • 2003
  • A series of 3'- and 4'-branched carbocyclic nucleosides 25, 26, 27, 28, 29 and 30 were synthesized starting from simple acyclic ketone derivatives. The construction of the required quaternary carbon was made using a [3,3]-sigmatropic rearrangement. In addition, the installation of a methyl group in the 3'-position was accomplished using a Horner-Wadsworth-Emmons (HWE) reaction with triethyl 2-phosphonopropionate. Bis-vinyl was successfully cyclized using a Grubbs' catalyst (Ⅱ). Natural bases (adenine, cytosine, uracil) were efficiently coupled with the use of a Pd(0) catalyst.

Synthesis of 1,4-Dihydropyridine-5-Formyl Derivatives (1,4-Dihydropyridine-5-Formyl 유도체의 합성)

  • Hong, You-Hwa;Suh, Jung-Jin
    • YAKHAK HOEJI
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    • v.33 no.5
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    • pp.290-295
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    • 1989
  • 2,6-Dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid methyl ester (1) was formylated to 2,6-dimethy-4-(3'-nitrophenyl)-5-formyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (2) in 76% yield. At the elevated temperature, 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-monomethyl ester (3) was also converted into compound 2 in 46% yield. The compound 2 was reduced to 2,6-dimethyl-4-(3'-nitrophenyl)-5-hydroxymethyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (4) in 91% yield. Compound 2 was reacted with triethyl phosphonoacetate to give 2,6-dimethyl-4-(3'-nitrophenyl)-5-(2-ethoxycarbonyl ethenyl)-1,4-dihydropyridine-3-carboxylic acid methyl ester (5) in 50% yield. Reaction between compound 2 and amines (methyl amine, ethylamine, methoxylamine, hydroxyl amine, phenyl hydrazine and 1-amino-4-methyl piperazine) gave six schiff bases 7a, 7b, 7c, 7e, 7f in 81%, 91%, 82%, 81%, 50% and 84% yield, respectively.

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Synthesis and X-ray Structure Analysis of (Z)-1-(4-Bromophenyl)-1-phenyl-2-(4-tert-butylphenyl)ethene ((Z)-1-(4-브로모페닐)-1-페닐-2-(4-tert-부틸페닐)에텐의 합성 및 X-선 구조분석)

  • Kim, Chul-Bae;Cho, Hyun-Jong;Lee, Sung-Kyung;Park, Kwangyong
    • Applied Chemistry for Engineering
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    • v.20 no.3
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    • pp.335-338
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    • 2009
  • As important intermediates for blue emitting materials of organic light-emitting diodes, bromotriphenylethylene derivatives for distrylarylenes are prepared by reactions of bromobenzophenone with benzylphosphonates. The reaction produces a 60 : 40 mixture of (Z)- and (E)-geometric isomers that are difficult to be resolved. The (Z)-isomer is successfully isolated by a selective recrystallization process using 2-propanol as a solvent. The X-ray structure analysis of (Z)-isomer shows that dihedral angles between tert-butylphenyl ring and bromophenyl ring and between bromophenyl ring and phenyl ring are $56.5(4)^{\circ}$ and $74.1(4)^{\circ}$, respectively.