The First Example of 4,7,8,9-Tetrahydrothieno-[2,3-d]Azocine Synthesis by Domino Reaction of 4-ARYL-4,5,6,7-Tetrahydrothieno[3,2-c]Pyridines with Activated Alkynes

被引:7
|
作者
Voskressensky, L. G. [1 ]
Borisova, T. N. [1 ]
Chervyakova, T. M. [1 ]
Matveeva, M. D. [1 ]
Galaktionova, D. V. [1 ]
Tolkunov, S. V. [1 ]
Tolkunova, V. S. [2 ]
Eresko, A. B. [2 ]
Varlamov, A. V. [1 ]
机构
[1] Peoples Friendship Univ Russia, Moscow 117198, Russia
[2] Ukrainian Acad Sci, LM Litvinenko Inst Phys Organ Chem & Coal Chem, UA-83114 Donetsk, Ukraine
基金
俄罗斯基础研究基金会;
关键词
activated alkynes; tetrahydrothieno[2,3-d]azocines; tetrahydrothieno[3,2-c]pyridines; tetrahydropyridine ring expansion domino reaction; DERIVATIVES; INHIBITORS;
D O I
10.1007/s10593-014-1597-x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1-Aryl-substituted tetrahydrothieno[3,2-N]pyridines easily undergo domino reactions with activated alkynes, giving good yields of the corresponding tetrahydrothieno[2,3-d]azocines. The reactions of 1-methyl-substituted tetrahydrothieno[3,2-N]pyridine were more complicated.
引用
收藏
页码:1338 / 1345
页数:8
相关论文
共 23 条
  • [1] The First Example of 4,7,8,9-Tetrahydrothieno-[2,3-d]Azocine Synthesis by Domino Reaction of 4-ARYL-4,5,6,7-Tetrahydrothieno[3,2-c]Pyridines with Activated Alkynes
    L. G. Voskressensky
    T. N. Borisova
    T. M. Chervyakova
    M. D. Matveeva
    D. V. Galaktionova
    S. V. Tolkunov
    V. S. Tolkunova
    A. B. Eresko
    A. V. Varlamov
    Chemistry of Heterocyclic Compounds, 2014, 50 : 1338 - 1345
  • [2] Transformations of 4,5,6,7-tetrahydrothieno[3,2-c]-and 1,2,3,4-tetrahydrobenzothieno[2,3-c]pyridines in reactions with alkynes activated by electron-withdrawing substituents
    Voskressensky, L. G.
    Borisova, T. N.
    Listratova, A. V.
    Sorokina, E. A.
    Tolkunov, S. V.
    Varlamov, A. V.
    RUSSIAN CHEMICAL BULLETIN, 2007, 56 (05) : 1041 - 1048
  • [3] Transformations of 4,5,6,7-tetrahydrothieno[3,2-c]-and 1,2,3,4-tetrahydrobenzothieno[2,3-c]pyridines in reactions with alkynes activated by electron-withdrawing substituents
    L. G. Voskressensky
    T. N. Borisova
    A. V. Listratova
    E. A. Sorokina
    S. V. Tolkunov
    A. V. Varlamov
    Russian Chemical Bulletin, 2007, 56 : 1041 - 1048
  • [4] AN EFFICIENT AND CONVENIENT SYNTHESIS OF 4,5,6,7-TETRAHYDROTHIENO[3,2-c]PYRIDINES BY A MODIFIED PICTET-SPENGLER REACTION VIA A FORMYLIMINIUM ION INTERMEDIATE
    Kitabatake, Michikazu
    Hashimoto, Aki
    Saitoh, Toshiaki
    Sano, Takehiro
    Mohri, Kunihiko
    Horiguchi, Yoshie
    HETEROCYCLES, 2010, 81 (08) : 1903 - 1921
  • [5] Synthesis, docking and ADMET prediction of novel 5-((5-substituted-1-H-1,2,4-triazol-3-yl) methyl)-4,5,6,7-tetrahydrothieno [3,2-c] pyridine as antifungal agents
    Sangshetti, Jaiprakash N.
    Khan, Firoz A. Kalam
    Chouthe, Rashmi S.
    Damale, Manoj G.
    Shinde, Devanand B.
    CHINESE CHEMICAL LETTERS, 2014, 25 (07) : 1033 - 1038
  • [6] Synthesis and Biological Evaluation of New Antitubulin Agents Containing 2-(3′,4′,5′-trimethoxyanilino)-3,6-disubstituted-4,5,6,7-tetrahydrothieno[2,3-c]pyridine Scaffold
    Romagnoli, Romeo
    Prencipe, Filippo
    Oliva, Paola
    Cacciari, Barbara
    Balzarini, Jan
    Liekens, Sandra
    Hamel, Ernest
    Brancale, Andrea
    Ferla, Salvatore
    Manfredini, Stefano
    Zurlo, Matteo
    Finotti, Alessia
    Gambari, Roberto
    MOLECULES, 2020, 25 (07):
  • [7] Synthesis and biological evaluation of 4,5,6,7-tetrahydrothieno[2,3-c]pyridine-based β-aminonitriles and their derivatives: β-amino carboxamides, (thio)ureas, and tetracycles
    Madacsi, Ramona
    Traj, Peter
    Hackler, Laszlo, Jr.
    Nagy, Lajos I.
    Kari, Beata
    Puskas, Laszlo G.
    Kanizsai, Ivan
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (02) : 635 - 652
  • [8] Synthesis and Crystal Structure of (E)-ethyl 6-benzyl-2-[(cyclopropylmethylamino)(4-fluorophenylamino)methyleneamino]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate ethanol monosolvate
    Chen Hong
    Liu Ming-Guo
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2012, 31 (07) : 959 - 964
  • [9] The reaction of tetrahydrochromeno[3,4-c]pyridines with activated alkynes. The first synthesis of tetrahydrochromeno[4,3-d]azocines
    Voskressensky, Leonid G.
    Kulikova, Larisa N.
    Gozun, Sergey V.
    Khrustalev, Victor N.
    Borisova, Tatiana N.
    Listratova, Anna V.
    Ovcharov, Maxim V.
    Varlamov, Alexey V.
    TETRAHEDRON LETTERS, 2011, 52 (32) : 4189 - 4191
  • [10] Synthesis of Isomeric Isothiazolo[4′,3′:4,5]- and Isothiazolo[4′,5′:4,5]thieno[3,2-b]pyrano[2,3-d]pyridines by Combination of Domino Reactions
    Shestopalov, Anatoliy M.
    Larionova, Natalia A.
    Fedorov, Alexander E.
    Rodinovskaya, Lyudmila A.
    Mortikov, Valery Yu.
    Zubarev, Andrey A.
    Bushmarinov, Ivan S.
    ACS COMBINATORIAL SCIENCE, 2013, 15 (10) : 541 - 545