Gold-catalyzed cascade C-C and C-N bond formation: synthesis of polysubstituted indolequinones and pyrroles

被引:35
作者
Abdukader, Ablimit [1 ,2 ]
Xue, Qicai [1 ]
Lin, Aijun [1 ]
Zhang, Ming [1 ]
Cheng, Yixiang [1 ]
Zhu, Chengjian [1 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China
[2] Xinjiang Univ, Sch Chem & Chem Engn, Urumqi 830046, Peoples R China
基金
高等学校博士学科点专项科研基金;
关键词
Gold catalysis; Cascade reaction; Pyrrole; Indolequinone; Enamine; FREE-RADICAL REACTIONS; EFFICIENT APPROACH; CARBONYL-COMPOUNDS; 2-AMINO-1,4-NAPHTHOQUINONES; INHIBITORS; ALKALOIDS; DERIVATIVES; CYCLIZATION; HETEROATOM; OXIDANT;
D O I
10.1016/j.tetlet.2013.08.100
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The combination of Ph3PAuCl and AgoTf was proven to be an efficient catalyst for the cascade C-C and C-N bond formation reactions from enamines and bromoquinones or nitroolefins. This protocol affords a straightforward method for the synthesis of polysubstituted indolequinones and pyrroles in good yields. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5898 / 5900
页数:3
相关论文
共 50 条
  • [31] Silver-catalyzed C-C bond formation with carbon dioxide: significant synthesis of dihydroisobenzofurans
    Sekine, Kohei
    Takayanagi, Ayano
    Kikuchi, Satoshi
    Yamada, Tohru
    CHEMICAL COMMUNICATIONS, 2013, 49 (96) : 11320 - 11322
  • [32] Synthesis of 3-Substituted Quinazolinones via C-N and C-C bond Cleavage of Enaminone
    Ambethkar, Sethurajan
    Kalaiselvi, Mariappan
    Padmini, Vediappen
    Bhuvanesh, Nattamai
    CHEMISTRYSELECT, 2017, 2 (19): : 5329 - 5332
  • [33] Synthesis of Isoquinolines via Rhodium(III)-Catalyzed Dehydrative C-C and C-N Coupling between Oximines and Alkynes
    Zhang, Xingping
    Chen, Dan
    Zhao, Miao
    Zhao, Jing
    Jia, Aiqun
    Li, Xingwei
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (05) : 719 - 723
  • [34] Cobalt-Catalyzed Stereospecific C-N/C-O Bond Formation of Oxiranes with Diaziridines
    Maharana, Prabhat K.
    Sarkar, Tanumay
    Kar, Subhradeep
    Purkayastha, Siddhartha K.
    Guha, Ankur K.
    Punniyamurthy, Tharmalingam
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13) : 9447 - 9458
  • [35] Copper-catalyzed Oxidative C-C, C-O, and C-N Bond Forming Reactions of Arylboronic Acids
    Shirakawa, Eiji
    Nishikawa, Ryo
    Uchiyama, Nanase
    Hata, Ippei
    Hayashi, Tamio
    CHEMISTRY LETTERS, 2013, 42 (03) : 269 - 271
  • [36] TMSCI-Mediated Synthesis of α,β-Unsaturated Amides via C-C Bond Cleavage and C-N Bond Formation of Propargyl Alcohols with Trimethylsilyl Azide
    Song, Xian-Rong
    Song, Bo
    Qiu, Yi-Feng
    Han, Ya-Ping
    Qiu, Zi-Hang
    Hao, Xin-Hua
    Liu, Xue-Yuan
    Liang, Yong-Min
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16) : 7616 - 7625
  • [37] Synthesis of Spirofurooxindoles via Phenyliodine(III) Bis(trifluoroacetate) (PIFA)-Mediated Cascade Oxidative C-O and C-C Bond Formation
    Sun, Desong
    Zhao, Xiaoyuan
    Zhang, Bobo
    Cong, Ying
    Wan, Xintong
    Bao, Mingmai
    Zhao, Xue
    Li, Bing
    Zhang-Negrerie, Daisy
    Du, Yunfei
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (08) : 1634 - 1638
  • [38] Autotandem Catalysis: Synthesis of Pyrroles by Gold-Catalyzed Cascade Reaction
    Ueda, Hirofumi
    Yamaguchi, Minami
    Kameya, Hiroshi
    Sugimoto, Kenji
    Tokuyama, Hidetoshi
    ORGANIC LETTERS, 2014, 16 (18) : 4948 - 4951
  • [39] Synthesis of Dibenzodiazepinones via Tandem Copper(I)-Catalyzed C-N Bond Formation
    Gawande, Sachin D.
    Kavala, Veerababurao
    Zanwar, Manoj R.
    Kuo, Chun-Wei
    Huang, Wen-Chang
    Kuo, Ting-Shen
    Huang, Hsiu-Ni
    He, Chiu-Hui
    Yao, Ching-Fa
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (11-12) : 2599 - 2608
  • [40] Copper(II) Bromide-Catalyzed C-C/C-N Bond-Forming Reactions: Synthesis of Pyrrole-Incorporated Triarylmethanes
    Rao, H. Surya Prakash
    Rao, A. Veera Bhadra
    Shanmugam, Sivakumar
    SYNTHETIC COMMUNICATIONS, 2015, 45 (23) : 2712 - 2717