• Title/Summary/Keyword: Stille reaction

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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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    • v.28 no.9
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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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    • v.20 no.3
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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

  • Yu, Dong Jin;Choe, Won U;Lee, Seok Jong;An, Gyo Han
    • Bulletin of the Korean Chemical Society
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    • v.17 no.2
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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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    • v.28 no.7
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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.

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

  • Woo, Yong-Ho;Lee, Hyo-Sang;Park, Sungnam;Choi, E-Joon;Kim, BongSoo
    • Polymer(Korea)
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    • v.39 no.1
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    • pp.71-77
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    • 2015
  • We synthesized a low band gap alternating copolymer containing electron-rich units (i.e. dithienosiloles and benzodithiophenes) and electron-deficient units (i.e. difluorobenzothiadiazoles) for high performance organic solar cells. The polymer was prepared by the Stille coupling reaction and characterized using $^1H$ NMR, GPC, TGA, UV-visible absorption spectroscopy, and cyclic voltammetry. Solar cells were fabricated in a structure of ITO/PEDOT:PSS/polymer: $PC_{70}BM/Al$ with five different blending ratios of polymer and $PC_{70}BM$ (1:1.5, 1:2, 1:3, 1:3.5 and 1:4 by weight ratio). The best efficiency was achieved from the 1:3 ratio of polymer and $PC_{70}BM$ in the photoactive layer, and TEM revealed that there is an optimal nanoscale phase separation between polymer and $PC_{70}BM$ in the 1:3 ratio blend film.

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

  • Do, Thu Trang;Ha, Ye Eun;Kim, Joo Hyun
    • Polymer(Korea)
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    • v.37 no.6
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    • pp.694-701
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    • 2013
  • A new copolymer named T-TI24T (poly((5,5-(2-butyl-5,6-bisdecyloxy-4,7-di-thiophen-2-yl-isoindole-1,3-dione))- alt-(2,5-thiophene))) based on phthalimide derivative and thiophene is synthesized by the Stille-coupling reaction. The polymer shows relatively high number average molecular weight of 86500 g/mol with good solubility in common organic solvents such as chloroform, 1,2-dichlorobenzene, and toluene and is thermally stable up to $380^{\circ}C$. Besides, it possesses a relatively low highest occupied molecular orbital (HOMO) energy level of -5.33 eV, promising the high open circuit voltage ($V_{oc}$) for photovoltaic applications. Active layer solution of polymer T-TI24T-as a donor and (6)-1-(3-(methoxycarbonyl)- {5}-1-phenyl[5,6]-fullerene (PCBM)-as an acceptor in different weight ratios is applied to fabricate the polymer solar cell devices. The ratio of polymer/PCBM affects the solar cell efficiency and the best performance exhibits in the device with polymer/PCBM = 1:3 (w/w), which shows a power conversion efficiency (PCE) of 0.199% and a $V_{oc}$ of 0.99 V, respectively. Even though the device shows the very low PCE, the $V_{oc}$ is higher than that of well known bulk heterojunction type solar cell based on P3HT:PC61BM (c.a. 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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    • v.34 no.7
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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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    • v.28 no.11
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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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    • v.26 no.8
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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.