Ruthenium-Catalyzed Regioselective C7-H Arylation of 2-(Het)aryl[1,2,4]triazolo[1,5-a]pyrimidines with Aryl Halides

被引:1
|
作者
Shepelenko, K. E. [1 ]
Gnatiuk, I. G. [1 ]
Chernyshev, V. M. [1 ]
机构
[1] Platov South Russian State Polytech Univ, Novocherkassk 346428, Russia
关键词
ruthenium catalysis; C-H arylation; 1,2,4]triazolo[1,5-a]pyrimidines; H BOND ACTIVATION; ENABLES; AMETOCTRADIN; POTENT;
D O I
10.1134/S1070428024060095
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Unusual direction of the C-H arylation of 2-(het)aryl[1,2,4]triazolo[1,5-a]pyrimidines with (het)aryl halides under catalysis by ruthenium(II) complexes has been revealed. The reaction involved activation of the C-7-H bond rather than the C-alpha-H bond of the (het)aryl substituent at C-2 of the triazolopyrimidine core. The arylation of 2-substituted [1,2,4]triazolo[1,5-a]pyrimidines with (het)aryl bromides afforded a series of 7-(het)aryl derivatives in good yields.
引用
收藏
页码:1042 / 1050
页数:9
相关论文
共 50 条
  • [1] SYNTHESIS OF 2-ARYL[1,2,4]TRIAZOLO[1,5-A]PYRIMIDINES
    KAMALA, K
    RAO, PJ
    REDDY, KK
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (10) : 3791 - 3793
  • [2] SYNTHESIS OF 2-ARYL-1,2,4-TRIAZOLO[1,5-A]PYRIMIDINES
    PRASAD, VSR
    REDDY, KK
    SYNTHETIC COMMUNICATIONS, 1990, 20 (17) : 2617 - 2622
  • [3] Direct C7-H Arylation of Pyrazolo[1,5-a]azines with Aryl Chlorides
    Nguyen, Thanh V. Q.
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (45)
  • [4] Direct (het)arylation of [1,2,4]triazolo[1,5-a]pyrimidines: Both eliminative and oxidative pathways
    Rasputin, Nikolay A.
    Demina, Nadezhda S.
    Irgashev, Roman A.
    Rusinov, Gennady L.
    Chupakhin, Oleg N.
    Charushin, Valery N.
    TETRAHEDRON, 2017, 73 (37) : 5500 - 5508
  • [5] Regioselective arylation of (het)aryl fragment in 2-(het)aryl-1-methylperimidines under ruthenium catalysis
    Shepelenko, Konstantin E.
    Gnatiuk, Irina G.
    Aleksandrov, Andrey A.
    Minyaev, Mikhail E.
    Chernyshev, Victor M.
    MENDELEEV COMMUNICATIONS, 2024, 34 (06) : 875 - 877
  • [6] SYNTHESIS OF 2-ARYL-[1,2,4]TRIAZOLO[1,5-A]PYRAZINES
    SAMBAIAH, T
    REDDY, KK
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1992, 31 (07): : 444 - 445
  • [7] SYNTHESIS OF 2-ARYL[1,2,4]TRIAZOLO[1,5-A]PYRAZINES
    SAMBAIAH, T
    REDDY, KK
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 57 - MEDI
  • [8] 2-aryl(hetaryl)-4H-[1,2,4]triazolo[1,5-a]benzimidazoles
    Morkovnik, A. S.
    Kuz'menko, T. A.
    Divaeva, L. N.
    Borodkin, G. S.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 49 (06) : 895 - 903
  • [9] Synthesis, photophysical and redox properties of the 2,5,7-tri(het)aryl-[1,2,4]triazolo[1,5-a]pyrimidines
    Rasputin, Nikolay A.
    Demina, Nadezhda S.
    Irgashev, Roman A.
    Shchepochkin, Alexander V.
    Rusinov, Gennady L.
    Chupakhin, Oleg N.
    Charushin, Valery N.
    ARKIVOC, 2020, : 330 - 342
  • [10] 2-aryl(hetaryl)-4H-[1,2,4]triazolo[1,5-a]benzimidazoles
    A. S. Morkovnik
    T. A. Kuz’menko
    L. N. Divaeva
    G. S. Borodkin
    Russian Journal of Organic Chemistry, 2013, 49 : 895 - 903