Synthesis of 7H-Indolo[2,3-c]quinolines by Chemoselective Suzuki Reaction Followed by a Ring-Closing Two-Fold Buchwald-Hartwig Reaction of 3-Bromo-4-iodoquinoline

被引：7
作者：
Rivera, Rodisnel Perdomo [1 ,3 ]
Ehlers, Peter [1 ,2 ]
Rodriguez, Eugenio Torres [3 ]
Langer, Peter [1 ,2 ]
机构：
[1] Univ Rostock, Inst Chem, A Einstein Str 3, D-18059 Rostock, Germany
[2] Univ Rostock, Leibniz Inst Katalyse eV, A Einstein Str 29a, D-18059 Rostock, Germany
[3] Univ Granma, Study Ctr Appl Chem, Carretera Manzanillo Km 1712, Bayamo 85100, Granma, Cuba
来源：
CHEMISTRYSELECT | 2018年 / 3卷 / 40期
关键词：
Chemoselectivity; Cross-coupling reactions; Heterocycles; Palladium; DOUBLE N-ARYLATION; CRYPTOLEPIS-SANGUINOLENTA; INDOLOQUINOLINE ALKALOIDS; ANTIPLASMODIAL ACTIVITY; ANTIMALARIAL ACTIVITY; CONVENIENT SYNTHESIS; PRIMARY AMINES; IN-VITRO; ISOCRYPTOLEPINE; DERIVATIVES;
D O I：
10.1002/slct.201802320
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
N-functionalized 7H-indolo[2,3-c]quinolines have been synthesized by chemoselective Suzuki-reaction followed by a ring-closing two-fold Buchwald-Hartwig reaction. The developed methodology allows the application of various anilines, benzyl amines as well as aliphatic amines and led to corresponding products in high yields.
引用
收藏
页码：11177 / 11179
页数：3
相关论文
共 32 条
  • [11] Heteroatom directed photoannulation: synthesis of indoloquinoline alkaloids: cryptolepine, cryptotackieine, cryptosanguinolentine, and their methyl derivatives
    Dhanabal, T.
    Sangeetha, R.
    Mohan, P. S.
    [J]. TETRAHEDRON, 2006, 62 (26) : 6258 - 6263
  • [12] Synthesis and Antiplasmodial Activity of Aminoalkylamino-Substituted Neocryptolepine Derivatives
    El Sayed, Ibrahim
    Van der Veken, Pieter
    Steert, Koen
    Dhooghe, Liene
    Hostyn, Steven
    Van Baelen, Gitte
    Lemiere, Guy
    Maes, Bert U. W.
    Cos, Paul
    Maes, Louis
    Joossens, Jurgen
    Haemers, Achiel
    Pieters, Luc
    Augustyns, Koen
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (09) : 2979 - 2988
  • [13] A short and convenient synthesis and evaluation of the antiinfective properties of indoloquinoline alkaloids:: 10H-Indolo[3,2-b]quinoline and 7H-indolo[2,3-c]quinolines
    Etukala, Jagan R.
    Kumar, E. V. K. Suresh
    Ablordeppey, Seth Y.
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (02) : 507 - 511
  • [14] Grellier P, 1996, PHYTOTHER RES, V10, P317, DOI 10.1002/(SICI)1099-1573(199606)10:4<317::AID-PTR858>3.0.CO
  • [15] 2-0
  • [16] Synthesis of 7H-indolo[2,3-c]quinolines:: Study of the Pd-catalyzed intramolecular arylation of 3-(2-bromophenylamino)quinolines under microwave irradiation
    Hostyn, S
    Maes, BUW
    Van Baelen, G
    Gulevskaya, A
    Meyers, C
    Smits, K
    [J]. TETRAHEDRON, 2006, 62 (19) : 4676 - 4684
  • [17] Synthesis of the benzo-β-carboline isoneocryptolepine:: the missing indoloquinoline isomer in the alkaloid series cryptolepine, neocryptolepine and isocryptolepine
    Hostyn, S
    Maes, BUW
    Pieters, L
    Lemiére, GLF
    Mátyus, P
    Hajós, G
    Dommisse, RA
    [J]. TETRAHEDRON, 2005, 61 (06) : 1571 - 1577
  • [18] Jung H. S., 2011, Patent: KR, Patent No. 2011105268
  • [19] IN-VITRO AND IN-VIVO ANTIMALARIAL ACTIVITY OF CRYPTOLEPINE, A PLANT-DERIVED INDOLOQUINOLINE
    KIRBY, GC
    PAINE, A
    WARHURST, DC
    NOAMESE, BK
    PHILLIPSON, JD
    [J]. PHYTOTHERAPY RESEARCH, 1995, 9 (05) : 359 - 363
  • [20] One-step construction of carbazoles by way of the palladium-catalyzed double N-arylation reaction and its application to the total synthesis of murrastifoline-A
    Kitawaki, Takafumi
    Hayashi, Yoko
    Ueno, Akiko
    Chida, Noritaka
    [J]. TETRAHEDRON, 2006, 62 (29) : 6792 - 6801
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