Synthesis of Indolizines via Palladium Catalyzed Annulation of Propargyl Carbonates and 2-(Pyridin-2-yl)acetonitrile Derivatives

被引:36
|
作者
Wu, Ting [1 ,2 ]
Chen, Min [1 ,2 ]
Yang, Yuzhu [1 ,2 ]
机构
[1] Guizhou Med Univ, State Key Lab Funct & Applicat Med Plants, 3491 Baijin Rd, Guiyang 550014, Guizhou, Peoples R China
[2] Chinese Acad Sci, Key Lab Chem Nat Prod Guizhou Prov, 3491 Baijin Rd, Guiyang 550014, Guizhou, Peoples R China
关键词
EFFICIENT SYNTHESIS; FUNCTIONALIZED INDOLIZINES; 1,3-DIPOLAR CYCLOADDITION; CASCADE; 2-ALKYLAZAARENES; CYCLIZATION; ACTIVATION; ARYLATION; ALKYNES; YLIDES;
D O I
10.1021/acs.joc.7b02278
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Pd-catalyzed regioselective annulation reaction of propargyl carbonates and 2-(pyridine-2-y1) acetonitrile derivatives has been accomplished, which provides a straightforward and efficient access to polysubstituted indolizines. The choice of the phosphine ligand is crucial to the high regio-selectivity of the reaction.
引用
收藏
页码:11304 / 11309
页数:6
相关论文
共 50 条
  • [31] Palladium-Catalyzed Regioselective Synthesis of 1,2-Fused Indole-Diazepines via [5+2] Annulation of o-Indoloanilines with Alkynes
    Thikekar, Tushar Ulhas
    Sun, Chung-Ming
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (19) : 3388 - 3396
  • [32] 2-Alkylindoles via palladium-catalyzed reductive cyclization of ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonates
    Ambrogio, Ilaria
    Cacchi, Sandro
    Fabrizi, Giancarlo
    TETRAHEDRON LETTERS, 2007, 48 (43) : 7721 - 7725
  • [33] A copper-catalyzed annulation reaction of diazo esters with propargyl amines for the synthesis of 2,5-dihydropyrroles
    Xie, Haodong
    Zhao, Wei
    Wei, Heping
    Yu, Yang
    Zhao, Lili
    Baell, Jonathan B.
    Huang, Fei
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (16): : 4546 - 4555
  • [34] Synthesis of indolines via palladium-catalyzed [4+1] annulation of (2-aminophenyl)methanols with sulfoxonium ylides
    Hao, Erxiao
    Kong, Xiaomei
    Xu, Tongyu
    Zeng, Fanlong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (31) : 6342 - 6351
  • [35] Cp*Co(III)-Catalyzed Regioselective Synthesis of Cyclopenta[b]carbazoles via Dual C(sp2)-H Functionalization of 1-(Pyridin-2-yl)-indoles with Diynes
    Li, Qiuyun
    Wang, Yanwei
    Li, Bin
    Wang, Baiquan
    ORGANIC LETTERS, 2018, 20 (24) : 7884 - 7887
  • [36] Copper-Mediated and Palladium-Catalyzed Cross-Coupling of Indoles and N-Methylpyridinium Salts: A Practical Way to Prepare 3-(Pyridin-2-yl)indoles
    Tang, Juan
    Li, Shun
    Zhang, Jing
    Yan, Mei-xin
    Shi, Yong-lin
    Zheng, Xue-li
    Yuan, Mao-lin
    Fu, Hai-yan
    Li, Rui-xiang
    Chen, Hua
    ORGANIC LETTERS, 2023, 25 (28) : 5203 - 5208
  • [37] Palladium-Catalyzed Annulation of 2,2′-Diiodobiphenyls with Alkynes: Synthesis and Applications of Phenanthrenes
    Lin, Yu-De
    Cho, Chun-Lung
    Ko, Chih-Wei
    Pulte, Anna
    Wu, Yao-Ting
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22) : 9979 - 9988
  • [38] Palladium-catalyzed intermolecular coupling of 3-substituted propargylic carbonates with phenols: Synthesis of 2-substituted benzofuran derivatives
    Watanabe, Hirotaka
    Okubo, Masataka
    Watanabe, Kouichi
    Udagawa, Takumi
    Kawatsura, Motoi
    TETRAHEDRON LETTERS, 2017, 58 (30) : 2893 - 2897
  • [39] Palladium-catalyzed carbonylation of 2-(propargyl)allyl phosphates leading to highly unsaturated γ-lactones
    Kamitani, A
    Chatani, N
    Murai, S
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (12) : 1397 - 1399
  • [40] Palladium-catalyzed synthesis of 2-allylindole and 2-allylbenzofuran derivatives from 2-((trimethylsilyl)ethynyl)arenes
    Chakraborty, Amrita
    Jyothi, Konanki
    Sinha, Surajit
    TETRAHEDRON LETTERS, 2014, 55 (50) : 6795 - 6798