Microwave-assisted synthesis of 5,6-dihydroindolo[1,2-a] quinoxaline derivatives through copper-catalyzed intramolecular N-arylation

被引：7
|
作者：
Zhao, Fei [1 ]
Zhang, Lei [1 ]
Liu, Hailong [1 ]
Zhou, Shengbin [1 ]
Liu, Hong [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 9卷
基金：
中国国家自然科学基金;
关键词：
copper; 5,6-dihydroindolo[1,2-a]quinoxaline; intramolecular N-arylation; microwave irradiation; INDOLE ALKALOIDS; HETEROCYCLES; CHEMISTRY; EFFICIENT; CASCADE; AMINES; MILD; CUI;
D O I：
10.3762/bjoc.9.285
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and practical protocol has been developed to synthesize 5,6-dihydroindolo[ 1,2-a] quinoxaline derivatives by CuI-catalyzed intramolecular N-arylation under microwave irradiation. This method rapidly afforded the tetracyclic products with good to excellent yields (83-97%) in short reaction times (45-60 min).
引用
收藏
页码：2463 / 2469
页数：7
相关论文
共 50 条
  • [31] Regioselective Synthesis of 1,2-and 1,4-Dihydroquinolines by Palladium-Catalyzed Intramolecular N-Arylation
    Park, Kyeong-Yong
    Lee, Jinyong
    Park, Seong Jun
    Heo, Jung-Nyoung
    Lim, Hwan Jung
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (18) : 3917 - 3926
  • [32] Synthesis of Pyrido[1,2-a]benzimidazoles through a Copper-Catalyzed Cascade C-N Coupling Process
    Wu, Zhiqing
    Huang, Qing
    Zhou, Xiangge
    Yu, Lintao
    Li, Zhengkai
    Wu, Di
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (27) : 5242 - 5245
  • [33] Microwave-assisted sequential one-pot protocol to benzothiadiazin-3-one-1,1-dioxides via a copper-catalyzed N-arylation strategy
    Rolfe, Alan
    Hanson, Paul R.
    TETRAHEDRON LETTERS, 2009, 50 (50) : 6935 - 6937
  • [34] Intramolecular N-arylation in heterocyclization: synthesis of new pyrido-fused pyrrolo[1,2-a][1,4]diazepinones
    Legeren, Loreto
    Dominguez, Domingo
    TETRAHEDRON LETTERS, 2010, 51 (31) : 4053 - 4057
  • [35] Microwave-Assisted Copper-Catalyzed Coupling of Bromoalkynes and Sulfonamides: Rapid Synthesis of N -Sulfonyl Ynamides
    Hong, Su Jeong
    Lee, Joon-Ho
    Yeom, Hyun-Suk
    SYNLETT, 2024, 35 (12) : 1436 - 1440
  • [36] Copper-Catalyzed One-Pot Synthesis of Pyrrolo[1,2-a]quinoxaline Derivatives from 1-(2-Aminophenyl)-pyrroles and Aldehydes
    Krishna, Thalishetti
    Reddy, Thatikonda Narendar
    Laxminarayana, Eppakayala
    Kalita, Dipak
    CHEMISTRYSELECT, 2019, 4 (01): : 250 - 253
  • [37] Copper-Catalyzed [5+1] Cyclization of o-Pyrrolo Anilines and Heterocyclic N-Tosylhydrazones for Access to Spiro-dihydropyrrolo[1,2-a]quinoxaline Derivatives
    Long, Yan
    Wang, Yun
    Chen, Yue-You
    Han, Wen-Yong
    Wan, Nan-Wei
    Yuan, Wei-Cheng
    Chen, Yong-Zheng
    Cui, Bao-Dong
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (06): : 4112 - 4123
  • [38] Microwave-assisted synthesis of pyrido[1,2-a]benzimidazole derivatives of β-aryloxyquinoline and their antimicrobial and antituberculosis activities
    Chetan B. Sangani
    Hardik H. Jardosh
    Manish P. Patel
    Ranjan G. Patel
    Medicinal Chemistry Research, 2013, 22 : 3035 - 3047
  • [39] Microwave-assisted synthesis of pyrido[1,2-a]benzimidazole derivatives of β-aryloxyquinoline and their antimicrobial and antituberculosis activities
    Sangani, Chetan B.
    Jardosh, Hardik H.
    Patel, Manish P.
    Patel, Ranjan G.
    MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (06) : 3035 - 3047
  • [40] Microwave-assisted synthesis of 1-aryl-1H-indazoles via one-pot two-step Cu-catalyzed intramolecular N-arylation of arylhydrazones
    Pabba, C
    Wang, HJ
    Mulligan, SR
    Chen, ZJ
    Stark, TM
    Gregg, BT
    TETRAHEDRON LETTERS, 2005, 46 (44) : 7553 - 7557
12345