• Title/Summary/Keyword: Pyrans

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Microwave-Assisted Solvent and Catalyst Free Synthesis of 2H-Pyrans

  • Edayadulla, Naushad;Lee, Yong Rok
    • Bulletin of the Korean Chemical Society
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    • v.34 no.10
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    • pp.2963-2967
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    • 2013
  • This paper describes a simple and efficient method involving domino Knovenegal/$6{\pi}$ electrocyclization for the preparation of a variety of 2H-pyrans using microwave irradiation under solvent- and catalyst-free conditions. This method offers the advantages of a green approach, high yields, and short reaction times. Sixteen compounds (9a-p) were obtained in good to excellent yields using the procedure.

Ring-Opening Polymerization of Substituted 3,4-Dihydro-2H-pyrans. Syntheses of Alternating Vinyl Copolymers of Dimethyl Dicyanofumarate and Electron-Rich Olefins

  • Lee, Ju-Yeon;Cho, I-Whan
    • Bulletin of the Korean Chemical Society
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    • v.7 no.5
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    • pp.372-376
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    • 1986
  • Substituted 3,4-dihydro-2H-pyrans ($1_{a-e}$) were prepared by (4 + 2) cycloaddition reaction of dimethyl dicyanofumarate with the corresponding electron-rich olefins. The compounds $1_{a-e}$ were ring-open polymerized by cationic initiators to obtain polymers of 1:1 alternating sequence. Polymerizations were carried out with boron trifluoride etherate in methylene chloride at $-78^{\circ}C$. All the polymers obtained were soluble in common solvents and were reprecipitated by pouring its chloroform solution into diethyl ether. All the compounds $1_{a-e}$ were not as reactive as the corresponding pyrans derived from ${\alpha}$ -cyanoacrylate.

One-Pot Synthesis of 2H-Pyrans by Indium(III) Chloride-Catalyzed Reactions.Efficient Synthesis of Pyranocoumarins, Pyranophenalenones, and Pyranoquinolinones

  • Lee, Yong-Rok;Kim, Do-Hoon;Shim, Jae-Jin;Kim, Seog K.;Park, Jung-Hag;Cha, Jin-Soon;Lee, Chong-Soon
    • Bulletin of the Korean Chemical Society
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    • v.23 no.7
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    • pp.998-1002
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    • 2002
  • An efficient synthesis of 2H-pyrans is achieved by indium (III) chloride-catalyzed reactions of 1,3-dicarbonyl compounds with a variety of $\alpha\beta-unsaturated$, aldehydes in moderate yields. This method has been applied to the synthesis of pyranocoumar ins, pyranophenalenones, and pyranoquinolinone alkaloids.

Efficient Synthesis of Bibenzyl Derivatives Bearing Pyranyl Moieties: First Total Synthesis of Bauhinol D

  • Park, Byung-Ho;Lee, Yong-Rok;Kim, Sung-Hong
    • Bulletin of the Korean Chemical Society
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    • v.32 no.2
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    • pp.566-570
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    • 2011
  • An efficient and general synthesis of bibenzyl derivatives bearing pyranyl rings was achieved by ethylenediamine diacetate-catalyzed reactions of 3,5-dihydroxybibenzyl with ${\alpha},{\beta}$-unsaturated aldehydes in moderate yields. These reactions provided naturally occurring compounds 1 and 2 in single step reaction. As an application of this methodology, biologically interesting natural bauhinol D (8) was synthesized by a convergent sequence from readily available benzaldehyde and benzyl phosphonate.

Synthesis of 3,4-Dihydro-2H-Pyran derivatives Utilizing Ag2CO3/Celite (Ag2CO3/Celite를 이용한 3,4-다이하이드로-2H-피란 유도체들의 합성)

  • Kim, Byung-So
    • Journal of the Korean Society of Industry Convergence
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    • v.9 no.4
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    • pp.331-336
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    • 2006
  • An efficient synthesis of 3,4-dihydro-2H-pyrans is achieved by $Ag_2CO_3$/celite mediated reaction of 1,3-dicarbonyl compounds with vinyl ether in moderate yields. This method has been applied to the synthesis of 3,4-dihydro-2H-pyranochromens and 3,4-dihydro-2H-benzochromen. 3,4-Dihydro-2H-pyranochromens were easily converted to 4H-pyranochromens by elimination of ethoxy group. The structures of these compound were identified by IR and $^1H$ NMR-Spectra.

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Red Fluorescent Organic Light-Emitting Diodes Using Modified Pyran-containing DCJTB Derivatives

  • Lee, Kum-Hee;Kim, Sung-Min;Kim, Jeong-Yeon;Kim, Young-Kwan;Yoon, Seung-Soo
    • Bulletin of the Korean Chemical Society
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    • v.31 no.10
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    • pp.2884-2888
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    • 2010
  • Two red fluorescent DCJTB derivatives (Red 1 and 2) based on modified pyrans were synthesized and their electroluminescent properties were investigated. Multilayered OLEDs were fabricated with the device structure of ITO/NPB (40 nm)/Red 1, 2 or DCJTB (0.5 or 1%): $Alq_3$ (20 nm)/$Alq_3$ (40 nm)/Liq (2 nm)/Al. All devices exhibited efficient red emissions. In particular, a device containing emitter Red 2 as a dopant in the emitting layer, the maximum luminance was $8737\;cd/m^2$ at 12.0 V, the luminous and power efficiencies were 2.31 cd/A and 1.25 lm/W at $20\;mA/cm^2$, respectively. The peak wavelength of the electroluminescence was 638 nm with the CIE (x,y) coordinates of (0.63, 0.36) at 7.0 V.

A Study on the fabrication and Characteristic Analysis of Organic Light Emitting Device using Inorganic Metal Multi-layer (무기금속 다층박막을 적용한 유기발광소자의 제작 및 특성 분석에 관한 연구)

  • Hwang, Soo-Woong;Kang, Seong-Jong;Cho, Jae-Young;Kim, Tae-gu;Oh, Hwan-Sool
    • Journal of the Korean Institute of Electrical and Electronic Material Engineers
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    • v.18 no.10
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    • pp.936-940
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    • 2005
  • IMML(Inorganic metal multi-layer) was used as cathode in the OLED devices to reduce the reflectance or ITO and increase the contrast ratio. Device structure was $ITO/{\alpha}-NPD/Alq_3:DCJTB/Alq_3/IMML/Al$. $Alq_3$ and DCJTB (4 - (dicyanomethylene) - 2 - ( 1 - propyls) 6 - methy 4H - pyrans) as host material lot red emission and red emitting guest material. IMML made three different layer: thin aluminum layer, aluminum layer doped with silicon monoxide, thick aluminum layer. The red OLED device with IMML showed the average reflectance of $4.97\%$, and then normal OLED with or without polarizer showed the average reflectance of $4.55\%$, $46\%$ at visible range from 380 nm to 780 nm. The brightness of OLED with IMML at 13 V was 5557 $cd/m^2$, and that of normal OLED with polarizer was 4872 $cd/m^2$. IMML could be the substitution for polarizer with same reflection, low cost, easy process in flat panel display market.