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
  • [21] Organotransition metal [3+2] cycloaddition reactions
    Frühauf, HW
    COORDINATION CHEMISTRY REVIEWS, 2002, 230 (1-2) : 79 - 96
  • [22] Theoretical studies of [3+2]-cycloaddition reactions
    Kuznetsov, M. L.
    USPEKHI KHIMII, 2006, 75 (11) : 1045 - 1073
  • [23] SYNTHESIS OF POLYCYCLIC RING-SYSTEMS VIA INTRAMOLECULAR [2+2]-CYCLOADDITION REACTIONS OF CYCLOPROPENE DERIVATIVES
    PADWA, A
    RIEKER, W
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1980, 180 (AUG): : 142 - ORGN
  • [24] Preparation, structure, and unique thermal [2+2], [4+2], and [3+2] cycloaddition reactions of 4-vinylideneoxazolidin-2-one
    Horino, Y
    Kimura, M
    Tanaka, S
    Okajima, T
    Tamaru, Y
    CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (11) : 2419 - 2438
  • [25] SYNTHESIS OF POLYCYCLIC RING-SYSTEMS VIA INTRAMOLECULAR [2+2]-CYCLOADDITION REACTIONS OF CYCLOPROPENE DERIVATIVES
    PADWA, A
    BLACKLOCK, TJ
    RIEKER, WF
    ISRAEL JOURNAL OF CHEMISTRY, 1981, 21 (2-3) : 157 - 163
  • [26] New Nazarov-[3+2]-cycloaddition cascade reactions.
    Giese, S
    Kastrup, L
    Stiens, D
    West, FG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U478 - U478
  • [27] Organocatalyzed Enantioselective [3+2] Cycloaddition Reactions for Synthesis of Dispiro[benzothiophenone-indandione-pyrrolidine] Derivatives
    Liu, Hong-Yan
    Du, Da-Ming
    MOLECULES, 2024, 29 (20):
  • [28] Synthesis and unusual [2+2] cycloaddition reactions of 1-trifluoroacetyl-2-haloacetylenes
    Tsvetkov, NP
    Koldobskii, AB
    Kalinin, VN
    DOKLADY CHEMISTRY, 2005, 404 (1-3) : 174 - 177
  • [29] [3+2] cycloaddition of diazomethane derivatives to perfluoro-2-phosphapropene
    Grobe, J
    Armbrecht, A
    Le Van, D
    Krebs, B
    Kuchinke, J
    Läge, M
    Würthwein, EU
    ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2001, 627 (06): : 1241 - 1247
  • [30] [3+2] Cycloaddition reactions of diethyl (E)-2-fluoromaleate
    Patrick, Timothy B.
    Shadmehr, Mehrdad
    Khan, Akbar H.
    Singh, Rajiv K.
    Asmelash, Bethel
    JOURNAL OF FLUORINE CHEMISTRY, 2012, 143 : 109 - 111
12345