Ruthenium-Catalyzed Pyrrole Synthesis via Oxidative Annulation of Enamides and Alkynes

被引:142
|
作者
Li, Bin [1 ]
Wang, Nuancheng [1 ]
Liang, Yujie [1 ]
Xu, Shansheng [1 ]
Wang, Baiquan [1 ,2 ]
机构
[1] Nankai Univ, State Key Lab Element Organ Chem, Coll Chem, Tianjin 300071, Peoples R China
[2] Chinese Acad Sci, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
H BOND ACTIVATION; REGIOSELECTIVE SYNTHESIS; SUBSTITUTED PYRROLES; EFFICIENT SYNTHESIS; CYCLIZATION; AMINES; FUNCTIONALIZATIONS; INDOLES; IMINES; COPPER;
D O I
10.1021/ol303159h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and regioselective ruthenium-catalyzed oxidative annulation of enamides with alkynes via the cleavage of C(sp(2))-H/N-H bonds is reported. The reactions can afford N-acetyl substituted or N-unsubstituted pyrroles by altering the reaction conditions slightly.
引用
收藏
页码:136 / 139
页数:4
相关论文
共 50 条
  • [1] Ruthenium-catalyzed annulation of alkynes with amides via formyl translocation
    Wu, Cui-Yan
    Hu, Ming
    Liu, Yu
    Song, Ren-Jie
    Lei, Yong
    Tang, Bo-Xiao
    Li, Rong-Jiang
    Li, Jin-Heng
    CHEMICAL COMMUNICATIONS, 2012, 48 (26) : 3197 - 3199
  • [2] Synthesis of Secondary Enamides by Ruthenium-Catalyzed Selective Addition of Amides to Terminal Alkynes
    Goossen, Lukas J.
    Salih, Kifah S. M.
    Blanchot, Mathieu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (44) : 8492 - 8495
  • [3] Ruthenium-Catalyzed Addition of Primary Amides to Alkynes: A Stereoselective Synthesis of Secondary Enamides
    Goossen, Lukas J.
    Blanchot, Mathieu
    Salih, Kifah S. M.
    Goosen, Kaethe
    SYNTHESIS-STUTTGART, 2009, (13): : 2283 - 2288
  • [4] Ruthenium-catalyzed benzimidazoisoquinoline synthesis via oxidative coupling of 2-arylbenzimidazoles with alkynes
    Kavitha, Nerella
    Sukumar, Genji
    Kumar, Vemula Praveen
    Mainkar, Prathama S.
    Chandrasekhar, Srivari
    TETRAHEDRON LETTERS, 2013, 54 (32) : 4198 - 4201
  • [5] Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides
    Alvarez-Perez, Andrea
    Esteruelas, Miguel A.
    Izquierdo, Susana
    Varela, Jesus A.
    Saa, Carlos
    ORGANIC LETTERS, 2019, 21 (13) : 5346 - 5350
  • [6] Synthesis of Botryllamides and Lansiumamides via Ruthenium-Catalyzed Hydroamidation of Alkynes
    Goossen, Lukas J.
    Blanchot, Mathieu
    Arndt, Matthias
    Salih, Kifah S. M.
    SYNLETT, 2010, (11) : 1685 - 1687
  • [7] Ruthenium-catalyzed oxidative cleavage of alkynes to carboxylic acids
    Yang, D
    Chen, F
    Dong, ZM
    Zhang, DW
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06): : 2221 - 2223
  • [8] Ruthenium-Catalyzed Oxidative Annulation and Hydroarylation of Chromene-3-carboxamides with Alkynes via Double C-H Functionalization
    Tulichala, R. N. Prasad
    Shankar, Mallepalli
    Swamy, K. C. Kumara
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (10): : 5068 - 5079
  • [9] Ruthenium-Catalyzed Oxidative Annulation of 6-Anilinopurines with Alkynes via C-H Activation: Synthesis of Indole-Substituted Purines/Purine Nucleosides
    Allu, Srinivasarao
    Swamy, K. C. Kumara
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (12) : 2665 - 2680
  • [10] Regioselective synthesis of isocoumarins by ruthenium-catalyzed aerobic oxidative cyclization of aromatic acids with alkynes
    Chinnagolla, Ravi Kiran
    Jeganmohan, Masilamani
    CHEMICAL COMMUNICATIONS, 2012, 48 (14) : 2030 - 2032