• Title/Summary/Keyword: Diels-Alder

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Synthesis of an Environmentally Friendly Phenol-Free Resin for Printing Ink

  • Ha, Young-Baeck;Jin, Ming Yu;Oh, Sung-Sang;Ryu, Do-Hyun
    • Bulletin of the Korean Chemical Society
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    • v.33 no.10
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    • pp.3413-3416
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    • 2012
  • Phenol-free resin was synthesized and its printing ink properties were investigated. The phenol-free resin was produced by esterification of poly phthalate and Diels-Alder adduct of rosin anhydride. Compared to rosin modified phenolic resin, eco-friendly phenol-free resin showed better vehicle properties in terms of gloss, yellowing, runability, and storage stability. The results suggest the utility of phenol-free resin instead of conventional rosin modified phenolic resin.

Synthesis of Arene-Fused Isoindoline Derivatives from Morita-Baylis-Hillman Adducts by IMDA Reaction Using Z-Vinylarenes as 1,3-Dienes

  • Kim, Ko Hoon;Lim, Jin Woo;Moon, Hye Ran;Kim, Jae Nyoung
    • Bulletin of the Korean Chemical Society
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    • v.35 no.11
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    • pp.3254-3260
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    • 2014
  • Intramolecular Diels-Alder (IMDA) reaction of vinylarenes bearing a Z-alkenyl tether, prepared from Morita-Baylis-Hillman (MBH) adducts, afforded arene-fused isoindoline derivatives in good yields. Vinylfurans, vinylthiophenes, and vinylnaphthalenes could be used successfully as dienes, while vinylbenzene failed under the same reaction conditions.

New Water-soluble Cutting Fluids Additives Derived from the Thermal Reaction Products of Unsaturated Fatty Acids with Acrylic Acid and Maleic Anhydride

  • Watanabe, Shoji
    • Journal of the Korean Applied Science and Technology
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    • v.20 no.4
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    • pp.372-376
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    • 2003
  • Water-soluble cutting fluids are used for processing of aluminium materials. This short article describes properties of new additives of water-soluble cutting fluids for aluminium materials. Various Diels-Alder adducts of unsaturated fatty acids with acrylic acid of maleic anhydride were prepared by thermal reactions. Triethanolamine salts of Diels-Alder adducts of dehydrated castor oil fatty acids with acrylic acid or maleic anhydride showed excellent anti-corrosion property of aluminium materals. These thermal adducts showed anti-rust property for cast-iron chips, too.

Synthesis and In vitro Evaluation of 4-Substituted-1-azaanthraquinones

  • Lee, Hee-Soon;Hong, Seoung-Soo;Choi, Jae-Young;Cho, Jung-Sook;Kim, Young-Ho
    • Archives of Pharmacal Research
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    • v.21 no.1
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    • pp.73-75
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    • 1998
  • In summary, six 4-substituted-1-azzanthraquinones were designed and synthesized using hetero Diels-Alder reaction as a key step. Although a great number of reaction conditions for benzylic bromination were examined, this step need to be improved for the efficient synthesis of the related analogues. 4-Bromomethyl-1-azzanthraquinone 6 may have potential for the treatment of tumors resistant to the doxorubicin. The compounds 9 and 10 containing the latent alkylating functionality may need further in depth biological evaluation. Work is in progress to design, synthesize, and evaluate additional compounds in this and related systems.

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Elucidation of Selectivity Difference in the Diels-Alder Reactions of 6,6-Disubstituted Cyclohexa-2,4-dienone

  • Jeong, Jun-Pyeong;Lee, Oh-Seuk;Yang, Ki-Yull
    • Bulletin of the Korean Chemical Society
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    • v.23 no.6
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    • pp.829-837
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    • 2002
  • Recently it was reported that cycloaddition of 6,6-disubstituted cyclohexa-2,4-dienone, 1 with cyclopentadiene gave solely the adduct of type 1.while its reaction with 1,3-cyclohexadiene gave both Ⅱ and Ⅲ. Semiempirical MO calculations were done to elucidate the origin of the selectivity difference between the two dienes. Cycloaddition of 1 with cyclopentadiene is controlled thermodynamically to give only 1-diene adduct by ΔGvalues of 10.6-20.3 kcal/mol, while its reaction with 1,3-cyclohexadiene does not show 1-diene/1-dienophile selectivity due to similar stabilities of the two adducts. Thermodynamic parameters also show that 두애 adducts are more fabourably fromed in the cycloadditions of 1 with both cyclopentadiene and 1,3-cyclohexadiene, which coincides with experimental observations. Cope rearrangements of endo adducts are another avenue to convert between 1-diene and 1-dienophile.

Synthesis of a New Diels-Alder Quinone Adduct and Its Use in Preparing Thiazolo- and Oxazoloquinolines

  • Hammam, A.S.;Youssef, M.S.K.;Radwan, Sh.M.;Abdel-Rahman, M.A.
    • Bulletin of the Korean Chemical Society
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    • v.25 no.6
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    • pp.779-785
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    • 2004
  • Syn (or anti) cinnamaldehydeoxime (1a, b) undergoes Diels-Alder addition to tetrabromo-p-benzoquinone (2)in dry xylene in 1 : 1 and 2 : 1 molar ratios to give the mono- and diadducts 3 and 4a, b respectively. The reaction of 3 with thioamides in ethanol gave thiazoloquinoline diones 6a-d, whereas with acid amides in ethylene glycol, it gave oxazoloquinolinediones 12a-f.

Synthesis of methyl 5-methylbicyclo (2.2-1)hept-2-ene-5- carboxylate via Diels-Alder Reaction (Diels-Alder 반응을 이용한 methyl 5-methylbicyclo(2-2.1)hept-2-ene-5-carboxylate의 합성)

  • Lee Yoon-Bae;Sung Si-Chang;Shin Eun-Jung;Ha Hong-Sik;Park Chan-Heung
    • Proceedings of the KAIS Fall Conference
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    • 2004.11a
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    • pp.265-268
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    • 2004
  • Methyl methacrlate와 cyclopentadiene을 반응하여 Methyl 5-methylbicyclo(2.2.1)hept-2-ene-5-carboxylate(MMBHC)를 합성코자 하였다. 합성된 MMBHC의 온도, solvent 변화와 촉매($AlCl_3$)의 사용 유무에 따른 endo, exe의 비율을 관찰하였다. 온도가 낮은 경우 온도가 높은 쪽 보다 endo 비율이 높았고 촉매($AlCl_3$)를 사용하였을 때(약 endo : exo = 63 : 37) 촉매를 사용하지 않은 반응(endo : exe = 34 : 66)보다 endo의 비율이 높았다. methyl acrylate를 사용한 경우 같은 조건에서 endo : exe의 비율이 93.5 : 6.5로 MMA를 사용한 경우보다 endo의 비율은 좋았다. 온도가 높은 경우 수율은 좋았지만 exe의 비율이 높았고 solvent에 따라 endo, exe의 선택도는 큰 차이를 보이지 않음을 알 수 있었다.

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Asymmetric Intramolecular Diels-Alder Cycloadditions of 2-Pyrone-3-Carboxylates and Synthesis of Vitamin $D_3$ A Ring Phosphine Oxide

  • 조천규;Gary H. Posner
    • Bulletin of the Korean Chemical Society
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    • v.19 no.9
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    • pp.957-961
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    • 1998
  • Intramolecular Diels-Alder cycloadditions of 2-pyrone-3-carboxylates with trans-vinyl silaketal groups tethered via a chiral, non-racemic 1,3-butanediol auxiliary proceeded in unexpected stepwise cycloadditions through ionic intermediates to provide cis-disubstituted bicylolactones. The ratio of two isomers, exo and endo, was 5 to 1, and each isomer was found to be diastereomerically pure (>99% de). Their relative and absolute stereochemistries were determined by $^1H$ NMR spectroscopy and confirmed by X-ray crystallography of minor, endo-adduct 9. The major exo-adduct was successfully transformed to (-)-2-butyl substituted A-ring phophine oxide 16, a key element for the synthesis of 2-butyl vitamin D3.