Synthesis of New Thienopyridine Derivatives by [3+2]- and [2+2]-Cycloaddition Reactions

被引:7
|
作者
Milen, Matyas [1 ,2 ]
Abranyi-Balogh, Peter [1 ]
Dancso, Andras [2 ]
Keglevich, Gyoergy [1 ]
机构
[1] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1521 Budapest, Hungary
[2] EGIS Pharmaceut PLC, Div Chem Res, H-1475 Budapest, Hungary
来源
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 22期
关键词
heterocycles; cycloadditions; nitrile oxides; nitrile imines; Staudinger reactions; NITRILE OXIDES; CYCLOADDITION REACTIONS; CLOPIDOGREL; NITRILIMINES; 3,4-DIHYDRO-BETA-CARBOLINES; 1,3-DIPOLES; TICLOPIDINE; STAUDINGER; PRECURSORS; REACTIVITY;
D O I
10.1055/s-0032-1316794
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of 6,7-dihydrothieno[3,2-c]pyridine derivatives with 1,3-dipoles, such as a nitrile oxides or nitrile imines, gave novel fused heterocycles. The Staudinger reaction of the starting material was also studied. This reaction was stereoselective and exclusively gave racemic cis-cycloadducts in which the thienopyridine core was fused with a beta-lactam ring.
引用
收藏
页码:3447 / 3452
页数:6
相关论文
共 50 条
  • [1] Catalytic [2+2] and [3+2] cycloaddition reactions of allenoates with cyclic ketimines
    Chen, Xiang-Yu
    Lin, Ruo-Chen
    Ye, Song
    CHEMICAL COMMUNICATIONS, 2012, 48 (09) : 1317 - 1319
  • [2] STEPWISE [2+2] AND [3+2] CYCLOADDITION REACTIONS OF ALLENYL CATIONS WITH OLEFINS
    MAYR, H
    SEITZ, B
    HALBERSTADTKAUSCH, IK
    JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (05): : 1041 - 1043
  • [3] Library Synthesis of Cyclobutanol Derivatives by Hyperbaric [2+2] Cycloaddition Reactions
    Janssen, Mathilde A. C. H.
    Rappard, Rico
    van Well, Michiel J.
    Blanco-Ania, Daniel
    Rutjes, Floris P. J. T.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (10)
  • [4] Synthesis and [3+2]-cycloaddition reactions of superelectrophilic (dimethylaminophenyl)benzofulvene derivatives
    Semenyuk, Yu P.
    Morozov, P. G.
    Kletskii, M. E.
    Burov, O. N.
    Cheprasov, A. S.
    Kurbatov, S. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 51 (03) : 449 - 451
  • [5] Comparative DFT study on the platinum catalyzed [3+2] and [2+2] cycloaddition reactions between the derivatives of allene and alkene
    Saha, Rohini
    Chatterjee, Arpita
    Mondal, Sonjoy
    Pal, Poulami
    Chakrabarty, Kuheli
    Das, Gourab Kanti
    COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2019, 1163
  • [6] Synthesis of new spiro pyrrole/pyrrolizine/thiazole derivatives via (3+2) cycloaddition reactions
    Mali, Prakash R.
    Khomane, Navnath B.
    Sridhar, B.
    Meshram, H. M.
    Likhar, Pravin R.
    NEW JOURNAL OF CHEMISTRY, 2018, 42 (16) : 13819 - 13827
  • [7] SYNTHESIS OF HETEROCYCLES BY THERMAL (2+2)-CYCLOADDITION REACTIONS OF ACETYLENES
    REINHOUDT, DN
    BULLETIN DES SOCIETES CHIMIQUES BELGES, 1981, 90 (06): : 633 - 643
  • [8] [2+2]-CYCLOADDITION AND [3+2]-CYCLOADDITION OF TRIISOPROPYLALLYLSILANE TO ALPHA,BETA-UNSATURATED BICYCLIC LACTAMS
    BRENGEL, GP
    RITHNER, C
    MEYERS, AI
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18): : 5144 - 5146
  • [9] COMPUTATIONAL MODELS OF SELECTIVE [3+2] CYCLOADDITION REACTIONS OF TRIMETHYLENEMETHANE DERIVATIVES
    ADEI, E
    HEHRE, W
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 208 : 60 - COMP
  • [10] [3+2] Cycloaddition Reactions to Indolyl- and Pyrrolyl Derivatives of Dinitrobenzofurazan
    Semenyuk, Yu. P.
    Kochubei, A. S.
    Morozov, P. G.
    Burov, O. N.
    Kletskii, M. E.
    Kurbatov, S. V.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2015, 50 (12) : 1731 - 1740