2-PHENYLPYRROLE: ONE-POT SELECTIVE SYNTHESIS FROM ACETOPHENONE OXIME AND ACETYLENE BY A TROFIMOV REACTION

被引:0
|
作者
Mikhaleva, A. I. [1 ]
Petrova, O. V. [1 ]
Sobenina, L. N. [1 ]
机构
[1] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, Irkutsk 664033, Russia
关键词
acetylene; acetophenone oxime; 2-phenylpyrrole; DERIVATIVES; ARYLATION;
D O I
10.1007/s10593-012-0922-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have developed a technologically orientated, one-pot way of synthesis of high purity 2-phenylpyrrole in 74% yield by treatment of acetophenone oxime with acetylene in the KOH-DMSO system. The reaction is carried out at 135-150 degrees C under an acetylene atmospheric pressure. The synthesis was performed in laboratory (glass apparatus) and in a large scale (10 l reaction vessel).
引用
收藏
页码:1367 / 1371
页数:5
相关论文
共 50 条
  • [1] 2-Phenylpyrrole: one-pot selective synthesis from acetophenone oxime and acetylene by a Trofimov reaction*
    A. I. Mikhaleva
    O. V. Petrova
    L. N. Sobenina
    [J]. Chemistry of Heterocyclic Compounds, 2012, 47 : 1367 - 1371
  • [2] A straightforward synthesis of pyrroles from ketones and acetylene: a one-pot version of the Trofimov reaction
    Schmidt, EY
    Mikhaleva, AI
    Vasil'tsov, AM
    Zaitsev, AB
    Zorina, NV
    [J]. ARKIVOC, 2005, : 11 - 17
  • [3] ONE-POT SYNTHESIS OF DIVINYLOXY PROPENES BY REACTION OF GLYCEROL WITH ACETYLENE
    TROFIMOV, BA
    MALYSHEVA, SF
    SIGALOV, MV
    VYALYKH, EP
    KALABIN, GA
    [J]. TETRAHEDRON LETTERS, 1984, 25 (38) : 4257 - 4258
  • [4] One-pot synthesis of oxime ethers from benzaldehyde or acetophenone, hydroxylamine salt, potassium hydroxide, and alkyl halides
    Li, CB
    Zhang, H
    Cui, Y
    Zhang, SM
    Zhao, ZY
    Choi, MCK
    Chan, ASC
    [J]. SYNTHETIC COMMUNICATIONS, 2003, 33 (04) : 543 - 546
  • [5] One-pot synthesis of benzylacetamide from oxime under ultrasound irradiation
    Li, Ji-Tai
    Meng, Xian-Tao
    Zhai, Xin-Li
    [J]. ULTRASONICS SONOCHEMISTRY, 2009, 16 (05) : 590 - 592
  • [6] Selective synthesis of 1-vinylpyrroles directly from ketones and acetylene: Modification of trofimov reaction
    A. I. Mikhaleva
    E. Yu. Shmidt
    A. V. Ivanov
    A. M. Vasil’tsov
    E. Yu. Senotrusova
    N. I. Protsuk
    [J]. Russian Journal of Organic Chemistry, 2007, 43 : 228 - 230
  • [7] Selective synthesis of 1-vinylpyrroles directly from ketones and acetylene: Modification of Trofimov reaction
    Mikhaleva, A. I.
    Shmidt, E. Yu.
    Ivanov, A. V.
    Vasil'tsov, A. M.
    Senotrusova, E. Yu.
    Protsuk, N. I.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 43 (02) : 228 - 230
  • [8] Chemoenzymatic one-pot reaction from carboxylic acid to nitrile via oxime
    Horvat, Melissa
    Weilch, Victoria
    Radisch, Robert
    Hecko, Sebastian
    Schiefer, Astrid
    Rudroff, Florian
    Wilding, Birgit
    Klempier, Norbert
    Patek, Miroslav
    Martinkova, Ludmila
    Winkler, Margit
    [J]. CATALYSIS SCIENCE & TECHNOLOGY, 2022, 12 (01) : 62 - 66
  • [9] One-pot synthesis of glycidyl propargyl ether from acetylene, formaldehyde, and epichlorohydrin
    Stankevich, VK
    Klimenko, GR
    Kukharev, BF
    Trofimov, BA
    [J]. RUSSIAN JOURNAL OF APPLIED CHEMISTRY, 2000, 73 (01) : 174 - 175
  • [10] Selective one-pot synthesis of various phenols from diarylethanes
    Nakamura, Ryota
    Obora, Yasushi
    Ishii, Yasutaka
    [J]. CHEMICAL COMMUNICATIONS, 2008, (29) : 3417 - 3419