Rhodium-catalyzed coupling of α-lactams with indole derivatives

被引:3
|
作者
Box, Hannah K. [1 ]
Kumarasinghe, K. G. Upul [1 ]
Nareddy, Radhika R. [1 ]
Akurathi, Gopalakrishna [1 ]
Chakraborty, Amarraj [1 ]
Raji, Babatunde [1 ]
Rowland, Gerald B. [1 ,2 ]
机构
[1] Mississippi State Univ, Dept Chem, Mississippi State, MS 39762 USA
[2] Univ Mississippi, Dept Chem & Biochem, University, MS 38677 USA
关键词
alpha-Lactams; C-N bond formation; Indo; CYCLOADDITION REACTIONS; ALKYLATION; COMPLEXES; AMINATION; ARYLATION;
D O I
10.1016/j.tet.2014.10.049
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report herein a method that allows for the formation of a C-N bond between the C-3 carbon of alactams and the nitrogen atom of indoles. A general procedure for the coupling of indoles and alpha-lactams in only 25 mm with high yield is reported. The scope of the reaction was extended by the development of a method for the in situ generation of less stable phenyl-substituted a-lactams. The developed method provides an atom-economical method for the formation of substituted a-amino amides that are found in a variety of biologically-active compounds. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9709 / 9717
页数:9
相关论文
共 50 条
  • [31] Rhodium-catalyzed coupling reaction of 2-vinylpyridines with allyl ethers
    Lim, YG
    Han, JS
    Koo, BT
    Kang, JB
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1999, 20 (09) : 1097 - 1100
  • [32] Rhodium-Catalyzed Decarboxylative and Dehydrogenative Coupling of Maleic Acids with Alkynes and Alkenes
    Itoh, Masaki
    Shimizu, Masaki
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (22): : 11427 - 11432
  • [33] Rhodium-Catalyzed Asymmetric Suzuki and Related Cross-Coupling Reactions
    Webster, Stephen
    Cunningham, Laura
    Fletcher, Stephen P.
    ALDRICHIMICA ACTA, 2024, 57 (01)
  • [34] Rhodium-catalyzed cross-coupling of aryl carbamates with arylboron reagents
    Nakamura, Keisuke
    Yasui, Kosuke
    Tobisu, Mamoru
    Chatani, Naoto
    TETRAHEDRON, 2015, 71 (26-27) : 4484 - 4489
  • [35] Rhodium-catalyzed coupling of arenes and fluorinated α-diazo diketones: synthesis of chromones
    Yao, Jiayi
    Kong, Lingheng
    Li, Xingwei
    CHEMICAL COMMUNICATIONS, 2020, 56 (86) : 13169 - 13172
  • [36] Rhodium-Catalyzed Cross-Coupling of Alkenyl Halides with Arylboron Compounds
    Matsuda, Takanori
    Suzuki, Kentaro
    Miura, Norio
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (17) : 3396 - 3400
  • [37] RHODIUM-CATALYZED COUPLING OF N-ALLYLAMIDES OF ORGANIC-ACIDS
    CHIUSOLI, GP
    COSTA, M
    PIVETTI, F
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 373 (03) : 385 - 389
  • [38] Rhodium-Catalyzed Allylation Reactions
    Thoke, Mahesh Bhagwan
    Kang, Qiang
    SYNTHESIS-STUTTGART, 2019, 51 (13): : 2585 - 2631
  • [39] RHODIUM-CATALYZED PHOTOCARBONYLATION OF HYDROCARBONS
    BOESE, WT
    ROSINI, GP
    ZHU, KM
    GOLDMAN, AS
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 298 - INOR
  • [40] Rhodium-catalyzed propargylic alkylations
    Lawler, Michael J.
    Evans, P. Andrew
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231