• 제목/요약/키워드: Stille reaction

검색결과 14건 처리시간 0.034초

An Efficient Synthesis of Risperidone via Stille Reaction: Antipsychotic, $5-HT_2$, and $Dopamine-D_2-Antagonist$

  • Kim Dong-myung;Kang Min-Seok;Kim Jeong Sook;Jeong Jin-Hyun
    • Archives of Pharmacal Research
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    • 제28권9호
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    • pp.1019-1022
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    • 2005
  • Risperidone has been reported to have neuroleptic activity. In this study, risperidone was synthesized using a new method involving a stille reaction, in which 2-methyl-3-vinyl-6,7,8,9-tet­rahydropyrido[1 ,2-a]pyrimidin-4-one was synthesized (5). The chemical synthesis process was found to be simple and produced risperidone in a high yield. In addition, can be easily scaled up for large scale synthesis.

An Efficient Synthesis of 3-(E)-Hydroxypropenyl Cephem Derivatives, Key intermediates for 3-(E)-Ammoniopro-penylcephalosporing Antibiotics

  • Lee, Yong-Sup;Lee, Jae-Yeol;Jeong, Jin-Hyun;Park, Hokoon
    • Archives of Pharmacal Research
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    • 제20권3호
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    • pp.288-290
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    • 1997
  • An efficient synthesis of 3-(E)-hydroxy- and 3-(E)-acetoxypropenylcephem derivatives, key intermediates for the synthesis of 3-(E)-propenylcephalosporins was achieved via Stille coupling reaction of 3-trifloxycephem with 3-(E)-tributylstannylallylic alcohol.

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A Synthetic Study on ($\pm$ )-Podosporin A

  • 유동진;최원우;이석종;안교한
    • Bulletin of the Korean Chemical Society
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    • 제17권2호
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    • pp.153-158
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    • 1996
  • The synthesis of common skeleton of podosporin A and aureol was studied through cationic olefin cyclization as a key step. The generation of thermodynamic silyl enol ether or enol acetate under known conditions gave regioselectivity of 88:12. The enolate alkylation of 2,3-dimethylcyclohexanone with 2,5-dimethoxybenzyl bromide at the more substituted site via lithium enolate gave poor yield. In this case an organozincate or an ammonium enolate also proved to be ineffective or not practical in terms of yield. Side chain elongation of the substituted cyclohexanone 13 through Grignard reaction, Wittig reaction, or Shappiro reaction did not proceed because of steric hindrance and side reactions. However, Stille coupling reaction via enol triflate produced the desired product 18 in high yield. The advanced intermediate 22, which was efficiently synthesized from 18, produced 24 instead of the desired product under a cationic olefin cyclization condition, indicating that the cyclization occurred in a stepwise mannervia the organomercury intermediate 23.

Synthesis and Properties of Hexyl End-Capped Thiophene Oligomers Containing Anthracene Moiety in the Center

  • Choi, Jung-Hei;Cho, Dae-Won;Jin, Sung-Ho;Yoon, Ung-Chan
    • Bulletin of the Korean Chemical Society
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    • 제28권7호
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    • pp.1175-1182
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    • 2007
  • A series of new organic semiconductors hexyl end-capped thiophene-anthracene oligomers containing the anthracene moiety in the center of the oligomers are synthesized. The target oligomers have been obtained by Stille coupling reactions as key step reactions. The synthesized thiophene-anthracene oligomers were characterized by 1H-NMR, 13C-NMR and high-resolution mass spectroscopy, respectively. All of the oligomers are soluble in chlorinated solvents. Their optical, thermal and electrochemical properties were measured. The hexyl end-capped oligomers and their unsubstituted oligomers exhibit the same absorption behavior in dilute toluene solution. Hexyl end-capped bis-terthienylanthracene oligomer is observed to show liquid crystalline mesophase at 166 oC in heating process. The thermal analyses as well as the electrochemical measurement data indicate that the designed materials show better thermal and oxidation stability than the corresponding oligothiophenes without anthracene core. Fluorescence lifetimes and fluorescence quantum yields of the thiophene-anthracene oligomers are measured to be 10-14 ps and 3.4-9.9 × 10?3 which are much shorter and lower than those of oligothiophenes respectively.

유기태양전지를 위한 작은 밴드갭 고분자의 합성과 광전특성 (Synthesis and Photovoltaic Properties of a Low Band Gap Polymer for Organic Solar Cell)

  • 우용호;이효상;박성남;최이준;김봉수
    • 폴리머
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    • 제39권1호
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    • pp.71-77
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    • 2015
  • 본 연구에서는 전자가 풍부한 구조단위(dithienosilole 및 benzodithiophene)와 전자가 부족한 구조단위(difluorobenzothiadiazole)를 주사슬에 교대로 갖는 작은 밴드갭 공중합체를 Stille 짝지움 반응을 이용하여 합성하였다. $^1H$ NMR을 통하여 각 단계별 화합물과 고분자의 구조를 확인하였다. GPC, TGA, UV-vis 분광분석기 및 cyclic voltammetry를 이용하여 합성한 고분자의 특성을 조사하였다. 합성한 공액고분자와 $PC_{70}BM$을 1:1.5, 1:2, 1:3, 1:3.5 및 1:4의 중량비로 혼합하여 ITO/PEDOT:PSS/polymer:$PC_{70}BM/Al$의 구조로 유기태양전지 소자를 제작하여 그 광전특성을 조사하였다. 고분자:$PC_{70}BM$의 혼합비율이 1:3에서 최고 1.0%의 광전변환효율이 달성되었다. TEM 실험을 통하여 1:3 혼합비율에서 유기태양전지에 가장 적합한 나노규모로 상분리가 일어났으며, 다른 혼합비율에서는 고분자와 $PC_{70}BM$의 뭉침현상에 기인하여 태양전지 특성이 낮아졌다.

프탈이미드 유도체를 기본으로 하는 공액고분자의 합성과 특성, 그리고 태양전지의 적용 (Synthesis and Characterization of π-Conjugated Polymer Based on Phthalimide Derivative and its Application for Polymer Solar Cells)

  • ;하예은;김주현
    • 폴리머
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    • 제37권6호
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    • pp.694-701
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    • 2013
  • 프탈이미드 유도체와 티오펜 단량체들을 이용하여 새로운 고분자인 poly((5,5-(2-butyl-5,6-bisdecyloxy-4,7-dithiophen-2-yl-isoindole-1,3-dione))-alt-(2,5-thiophene))(T-TI24T)를 Stille법을 이용하여 합성하였다. T-TI24T의 수평균 분자량은 86500 g/mol로 매우 높으며 클로로포름, 1,2-디클로로벤젠, 톨루엔과 같은 용매에 매우 잘 용해된다. 또한 $380^{\circ}C$까지 매우 우수한 열적 안정성을 갖고 있다. T-TI24T는 꽤 낮은 호모에너지 준위(-5.33 eV)를 갖고 있다. 서로 다른 T-TI24T와 (6)-1-(3-(methoxycarbonyl)-{5}-1-phenyl[5,6]-fullerene(PCBM)의 무게비를 갖는 블렌드를 광활성층으로 하는 태양전지를 제작하여 특성을 살펴본 결과 고분자와 PCBM의 비율이 1:3일 때 가장 최적화된 결과를 보였으며, 이 때 광전변환 효율과 개방전압은 각각 0.199%와 0.99였다. T-TI24T 기반 태양전지들은 비록 매우 작은 광전변환 효율을 갖지만 잘 알려진 P3HT:PC61BM으로 구성된 태양전지와 비교해 큰 매우 큰 개방전압을 갖는다(약 0.5 V).

Ligand Effect in Recycled CNT-Pd Heterogeneous Catalyst for Decarboxylative Coupling Reactions

  • Kim, Ji Dang;Pyo, Ayoung;Park, Kyungho;Kim, Gwui Cheol;Lee, Sunwoo;Choi, Hyun Chul
    • Bulletin of the Korean Chemical Society
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    • 제34권7호
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    • pp.2099-2104
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    • 2013
  • We present here an efficient and simple method for preparation of highly active Pd heterogeneous catalyst (CNT-Pd), specifically by reaction of dichlorobis(triphenylphosphine)palladium ($Pd(PPh_3)_2Cl_2$) with thiolated carbon nanotubes (CNTs). The as-prepared CNT-Pd catalysts demonstrated an excellent catalytic activity for the carbon-carbon (C-C) cross-coupling reactions (i.e. Suzuki, Stille, and decarboxylative coupling reactions) under mild conditions. The CNT-Pd catalyst could easily be removed from the reaction mixture; additionally, in the decarboxylative coupling of iodobenzene and phenylpropiolic acid, it showed a six-times recyclability, with no loss of activity. Moreover, once its activity had decreased by repeated recycling, it could easily be reactivated by the addition of phosphine ligands. The remarkable recyclability of the decarboxylative coupling reaction is attributable to the high degree of dispersion of Pd catalysts in CNTs. Aggregation of the Pd catalysts is inhibited by their strong adhesion to the thiolated CNTs during the chemical reactions, thereby permitting their recycling.

Synthesis and Properties of Soluble and Stable Silyl End-capped Bis-thienylanthracene Oligomers

  • Choi, Jung-Hei;Cho, Dae-Won;Sung, Nam-Kyoung;Jin, Sung-Ho;Yoon, Ung-Chan
    • Bulletin of the Korean Chemical Society
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    • 제28권11호
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    • pp.1931-1938
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    • 2007
  • Analyzed are recent advances in design of novel boronared conjugates of synthetic and natural porphyrins and chlorins. These compounds showed high efficacy as cytotoxic agents for tumor cells in culture and as phototoxins in photodynamic therapy of tumor xenografts. Thus, boronated porphyrins and chlorins emerge as promising class of anticancer agents with potentially multiple advantages: the chemotherapeutic drugs alone and photo- and radiosensitizers in binary treatments.

Synthesis and $PGE_2$ Inhibitory Activity of Vinylated and Allylated Chrysin Analogues

  • Dao, Tran-Thanh;Oh, Jeong-Won;Chi, Yeon-Sook;Kim, Hyun-Pyo;Sin, Kwan-Seog;Park, Hae-Il
    • Archives of Pharmacal Research
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    • 제26권8호
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    • pp.581-584
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    • 2003
  • Vinylated and allylated chrysin analogues were prepared as congeners of prenylated flavonoids and evaluated their anti-inflammatory activity. 8-Substituted chrysin analogues were prepared from 2 -hydroxy-3 -iodo-4 ,6 -dimethoxyacetophenone in 3 steps. 3-Allylated chrysin analogues were prepared from chrysin in 3 steps. Synthesized chrysin analogues (4, 5 and 8) showed moderate inhibitory activities of $PGE_2$ production from LPS-induced RAW 264.7 cells.