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] APPLICATION OF [3+2]-CYCLOADDITION IN THE SYNTHESIS OF VALDECOXIB
    Reddy, Anumula Raghupathi
    Goverdhan, Gilla
    Sampath, Aalla
    Mukkanti, Khagga
    Reddy, Padi Pratap
    Bandichhor, Rakeshwar
    SYNTHETIC COMMUNICATIONS, 2012, 42 (05) : 639 - 649
  • [2] Synthesis and in vivo antidiabetic activity of novel dispiropyrrolidines through [3+2] cycloaddition reactions with thiazolidinedione and rhodanine derivatives
    Murugan, Ramalingam
    Anbazhagan, S.
    Narayanan, S. Sriman
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (08) : 3272 - 3279
  • [3] (3+2)-Cycloaddition Reactions of Oxyallyl Cations
    Wu, Jimmy
    SYNTHESIS-STUTTGART, 2015, 47 (01): : 22 - 33
  • [4] Facile Dearomatization of Nitroquinolines through [3+2] and [4+2] Cycloaddition Reactions
    Bastrakov, Maxim A.
    Starosotnikov, Alexey M.
    Kachala, Vadim V.
    Fedyanin, Ivan V.
    Shevelev, Svyatoslav A.
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (02) : 146 - 153
  • [5] [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
  • [6] Synthesis of 2H-Indazoles by the [3+2] Cycloaddition of Arynes and Sydnones
    Wu, Chunrui
    Fang, Yuesi
    Larock, Richard C.
    Shi, Feng
    ORGANIC LETTERS, 2010, 12 (10) : 2234 - 2237
  • [7] Enantioselective Dearomative [3+2] Cycloaddition Reactions of Benzothiazoles
    Wang, Dong-Chao
    Xie, Ming-Sheng
    Guo, Hai-Ming
    Qu, Gui-Rong
    Zhang, Meng-Cheng
    You, Shu-Li
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (45) : 14111 - 14115
  • [8] Enantioselective Synthesis of Alkylthioetherpyrrolidine Derivatives via [3+2] Cycloaddition of α-Thioacrylates with Isocyanoacetates
    Wang, Zhi-Peng
    Li, Zi-Rui
    Wu, Qi
    Peng, Xiao-Jiao
    Shao, Pan-Lin
    He, Yun
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (23) : 12869 - 12876
  • [9] Synthesis of 3,4-Disubsituted Isoxazoles via Enamine [3+2] Cycloaddition
    Jia, Qian-fa
    Benjamin, Pooi Ming Shurn
    Huang, Jiayao
    Du, Zhiyun
    Zheng, Xi
    Zhang, Kun
    Conney, Allan H.
    Wang, Jian
    SYNLETT, 2013, 24 (01) : 79 - 84
  • [10] Synthesis of Fused Indoline-Cyclobutanone Derivatives via an Intramolecular [2+2] Cycloaddition
    Neyyappadath, Rifahath M.
    Greenhalgh, Mark D.
    Cordes, David B.
    Slawin, Alexandra M. Z.
    Smith, Andrew D.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (31-32) : 5169 - 5174
12345