Synthesis of 4-Oxoindeno[1,2-b]pyrroles through Copper-Catalyzed Tandem Reactions of 1-(2-Haloaryl)enones with Isocyanides

被引:7
|
作者
Zhou, Fengtao
Fu, Liangbing
Wie, Jiajia
Ding, Ke
Cai, Qian [1 ]
机构
[1] Chinese Acad Sci, Key Lab Regenerat Biol, Guangzhou Inst Biomed, Guangzhou 510530, Guangdong, Peoples R China
来源
SYNTHESIS-STUTTGART | 2011年 / 18期
关键词
copper-catalyzed; isocyanide; enones; pyrroles; ASYMMETRIC ALDOL REACTION; OLIGOSUBSTITUTED PYRROLES; CROSS-CYCLOADDITION; CARBONYL-COMPOUNDS; ISOCYANOACETATE; ALDEHYDES; COMPLEX; DERIVATIVES; ACETYLENES; AGONISTS;
D O I
10.1055/s-0030-1260171
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper-catalyzed tandem reactions of 1-(2-haloaryl)enones with isocyanides for the synthesis of 4-oxoindeno[1,2-b]pyrroles are described. Highly reactive cyclic organocopper intermediates are generated in the copper-catalyzed [3+2]-cycloaddition reactions of isocyanides to double or triple bonds. Successful intramolecular trapping of the organocopper intermediates led to the efficient formation of 4-oxoindeno[1,2-b]pyrroles.
引用
收藏
页码:3037 / 3044
页数:8
相关论文
共 50 条
  • [1] Copper-Catalyzed Tandem Reactions of 1-(2-Iodoary)-2-yn-1-ones with Isocyanides for the Synthesis of 4-Oxo-indeno[1,2-b]pyrroles
    Cai, Qian
    Zhou, Fengtao
    Xu, Tianfeng
    Fu, Liangbing
    Ding, Ke
    ORGANIC LETTERS, 2011, 13 (02) : 340 - 343
  • [2] Copper-Catalyzed Tandem Reaction of Isocyanides with N-(2-Haloaryl)propiolamides for the Synthesis of Pyrrolo[3,2-c]quinolin-4-ones
    Zhou, Fengtao
    Liu, Jianguang
    Ding, Ke
    Liu, Jinsong
    Cai, Qan
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (13) : 5346 - 5353
  • [3] Copper-Catalyzed Synthesis of Polysubstituted Pyrroles through [3+1+1] Cycloaddition Reaction of Nitrones and Isocyanides
    Tian, Zhuang
    Xu, Jiaojiao
    Liu, Bingxin
    Tan, Qitao
    Xu, Bin
    ORGANIC LETTERS, 2018, 20 (09) : 2603 - 2606
  • [4] Copper-catalyzed tandem aerobic oxidative cyclization for the synthesis of 4-cyanoalkylpyrrolo[1,2-a]quinoxalines from 1-(2-aminophenyl)pyrroles and cyclobutanone oxime esters
    An, Zhenyu
    Jiang, Yong
    Guan, Xin
    Yan, Rulong
    CHEMICAL COMMUNICATIONS, 2018, 54 (76) : 10738 - 10741
  • [5] 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
  • [6] Copper-catalyzed radical reactions of 2-azido-N-arylacrylamides with 1-(trifluoromethyl)1,2-benziodoxole and 1-azidyl-1,2-benziodoxole
    Yang, Tonghao
    Zhu, Haizhen
    Yu, Wei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (13) : 3376 - 3384
  • [7] A One-Pot Copper(II)-Catalyzed Tandem Synthesis of 2-Substituted Pyrrolo[1,2-b]pyridazin-4(1H)-ones
    Tan, Cun
    Xiang, Haoyue
    He, Qian
    Yang, Chunhao
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (17) : 3656 - 3660
  • [8] Copper-Catalyzed Cascade Synthesis of [1,2,4]-Triazoloquinazolinones
    Lou, Zhenbang
    Man, Ningning
    Yang, Haijun
    Zhu, Changjin
    Fu, Hua
    SYNLETT, 2018, 29 (10) : 1395 - 1399
  • [9] A Simple and Efficient Synthesis of Highly Substituted Indeno[1,2-b]pyrrole and Acenaphtho[1,2-b]pyrrole Derivatives by Tandem Three-Component Reactions
    Tang, Xiaodong
    Zhu, Songlei
    Ma, Ying
    Wen, Ren
    Cen, Lanqi
    Gong, Panwei
    Wang, Jing
    MOLECULES, 2018, 23 (11):
  • [10] Copper-Catalyzed Decarboxylative Three-Component Reactions for the Synthesis of Imidazo[1,2-α]pyridines
    Palani, Thiruvengadam
    Park, Kyungho
    Kumar, Manian Rajesh
    Jung, Hyun Ming
    Lee, Sunwoo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (26) : 5038 - 5047