• 제목/요약/키워드: intramolecular reaction

검색결과 145건 처리시간 0.024초

Approach to the Total Synthesis of Acanthoside-D

  • Ngoc, Thyen-Truong;Park, Hae-Il
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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    • pp.186.4-187
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    • 2003
  • Acanthoside-D, one of major components of Acanthopanacis Cortex, is known as a ginseng-like substance. it has been known to possess diverse biological effects. Acanthoside-D has a furofuran lignan structure and the synthesis of which poses interesting and often unsolved proplems of stereocontrol. Although a few interesting syntheses providing this natural product have been reported, an intermolecular McMurry coupling - intramolecular Mitsunobu cyclization route has not yet been explored. We report here a short and efficient synthetic pathway to the total synthesis of Acanthoside-D from aryl aldehydes and methyl acrylates via Baylis-Hillman reaction, intermolecular McMurry coupling and intramolecular Mitsunobu cyclization as key reaction.

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An Intramolecular Photosubstitution Reaction of N-(2,4-Dibromonaphthyl)- arenecarboxamide: Synthesis of 2-Arylnaphthoxazole

  • Bae, In-Soo;Kim, Yoo-Shin;Park, Yong-Tae
    • Bulletin of the Korean Chemical Society
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    • 제24권7호
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    • pp.916-920
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    • 2003
  • Photoreactions of N-(2,4-dibromonaphthyl)arenecarboxamides in basic medium result in the intramolecular substituted products, 2-aryl-8-bromonaphthoxazoles in moderate yields and further photoreactions of the products afford the reduced products, 2-arylnaphthoxazoles. These reactions are straightforward for syntheses of naphthoxazole derivatives. Since the intramolecular photosubstitution of the bromoarenecarboxamide by the oxygen of its amide group is more effective than the photoreduction of the substituted product, 2-aryl-8- bromonaphthoxazole in basic medium, the intramolecular substituted product, 2-aryl-8-bromonaphthoxazole can be isolated. A charge-transfered excited singlet state of an imidol form of the 2-bromoarenecarboxamide is involved in the photosubstitution, whereas an excited triplet state of the 2-aryl-8-bromonaphthoxzole is closely involved in the photoreduction.

Synthesis rind Reactions of Silacyclopropene or 1-Sila-1,2-Propadiene

  • Park, Seung-Ki
    • Journal of Photoscience
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    • 제9권1호
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    • pp.1-4
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    • 2002
  • This brief review deals with the thermal or photochemical synthesis and reactions of silacyclopropene or 1-sila-1,2-propadiene. The novel intramolecular reactions of silacyclopropene or 1-sila-1,2-propadiene are also discussed.

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Time-resolved Anisotropy Study on the Excited-State Intramolecular Proton Transfer of 1-Hydroxyanthraquinone

  • Choi, Jun-Rye;Jeoung, Sae-Chae;Cho, Dae-Won
    • Bulletin of the Korean Chemical Society
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    • 제24권11호
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    • pp.1675-1679
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    • 2003
  • The photodynamics of excited-state intramolecular proton transfer reaction of 1-hydroxyanthraquinone (1-HAQ) and 1-deuterioanthraquinone was investigated in toluene with time-resolved emission and femtosecond transient transmittance techniques at room temperature. The temporal profiles of transient transmittance of 1-HAQ could be well described with multi-decaying time constants. The ultrafast time constant within ca. 260 fs reflects the dynamics of proton transfer. The decay component of 2 ps is assigned to an additional proton translocation process induced by the intramolecular vibrational relaxation, whereas the decay component of 18 ps is assigned to the vibrational cooling process, while the long component (200 ps) can be explained in terms of the relaxation from excited-state keto-tautomer to its ground state. Time-resolved anisotropy decay dynamics and isotope effects on the photodynamics reveals that the ESIPT from enol-tautomer to keto-one of 1-HAQ is barrierless reaction and coupled to a vibrational relaxation process.

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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    • 제35권11호
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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.

The Link Between Stereoselectivity and Spin Selectivity in Intermolecular and Intramolecular Photochemical Reactions

  • Griesbeck, Axel G.
    • Journal of Photoscience
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    • 제10권1호
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    • pp.49-60
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    • 2003
  • How stereo selectivity in singlet and triplet photocycloaddition and photocyclization reactions, respectively, is linked to spin selectivity and how this link affects our understanding of photochemical reaction mechanisms, is described in this review. As illustrative examples, the Paterno-Buchi reaction and the Norrish-Yang cyclization are described with emphasis on triplet biradical structure and dynamics.

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Application of Excited-State Intramolecular Proton Transfer (ESIPT) Principle to Functional Polymeric Materials

  • Park, Sang-Hyuk;Kim, Se-Hoon;Seo, Jang-Won;Park, Soo-Young
    • Macromolecular Research
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    • 제16권5호
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    • pp.385-395
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    • 2008
  • Synthesis and properties of novel excited-state intramolecular proton transfer (ESIPT) materials, recently developed in our group, are described. Highly efficient ESIPT reaction, achieved in polyquinolines, polybenzoxazoles, and oxadiazole and imidazole derivatives possessing an intramolecular tautomerizable hydrogen bond, has been investigated theoretically and experimentally. It is demonstrated that unique properties arising from the ESIPT process (large Stokes' shift, no self-absorption, and easy population inversion, etc.) make it possible to produce advanced polymer devices for lasing, optical storage, and electroluminescence.