Quantum Mechanical Prediction and Experimental Verification of Au(I)-Catalyzed Substitution-Controlled Syntheses of 1H-Pyrido[4,3-b]indole and Spiro[indoline-3,3?-pyridine] Derivatives

被引:3
作者
Zhu, Jiang [1 ,2 ,3 ]
Li, Jiaji [1 ,2 ,3 ]
Zhang, Lianjie [1 ,2 ,3 ]
Sun, Shitao [1 ,2 ,3 ]
Wang, Zhaobo [1 ,2 ,3 ]
Li, Xiang [1 ,2 ,3 ]
Yang, Lu [1 ,2 ,3 ]
Cheng, Maosheng [1 ,2 ,3 ]
Lin, Bin [1 ,2 ,3 ]
Liu, Yongxiang [1 ,2 ,3 ]
机构
[1] Shenyang Pharmaceut Univ, Key Lab Struct Based Drug Design, Discovery Minist Educ, Shenyang 110016, Peoples R China
[2] Shenyang Pharmaceut Univ, Wuya Coll Innovat, Shenyang 110016, Peoples R China
[3] Inst Drug Res Med Capital China, Benxi 117000, Peoples R China
基金
中国国家自然科学基金;
关键词
HOMOGENEOUS GOLD CATALYSIS; INDUSTRIAL PERSPECTIVE; TANDEM CYCLIZATIONS; INDOLE ALKALOIDS; COUNTER ANIONS;
D O I
10.1021/acs.joc.2c03104
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Density functional theory calculations were applied to predict the pathways of gold(I)-catalyzed cycloisomerization of the indole substrates with 1,6-enynes, which were consistent with the ensuing experimental results. The substitution-controlled synthesis led to the formation of 1H-pyrido[4,3-b]indole and spiro[indoline-3,3 '-pyridine] derivatives in a tunable way. The reactions had good functional group tolerances, and a possible mechanism was proposed based on the computational and experimental results.
引用
收藏
页码:5483 / 5496
页数:14
相关论文
共 49 条
  • [1] Recent advances in spirocyclization of indole derivatives
    Bariwal, Jitender
    Voskressensky, Leonid G.
    Van der Eycken, Erik V.
    [J]. CHEMICAL SOCIETY REVIEWS, 2018, 47 (11) : 3831 - 3848
  • [2] Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes
    Campeau, Dominic
    Rayo, David F. Leon
    Mansour, Ali
    Muratov, Karim
    Gagosz, Fabien
    [J]. CHEMICAL REVIEWS, 2021, 121 (14) : 8756 - 8867
  • [3] Synthesis of Carbolines via Palladium/Carboxylic Acid Joint Catalysis
    Cera, Gianpiero
    Lanzi, Matteo
    Balestri, Davide
    Della Ca, Nicola
    Maggi, Raimondo
    Bigi, Franca
    Malacria, Max
    Maestri, Giovanni
    [J]. ORGANIC LETTERS, 2018, 20 (11) : 3220 - 3224
  • [4] Ag(i)/PPh3-catalyzed diastereoselective syntheses of spiro[indole-3,4′-piperidine] derivatives via cycloisomerizations of tryptamine-ynamides
    Chen, Yanyu
    Wang, Zhaobo
    Zhao, Wutong
    Sun, Shitao
    Yang, Lu
    Zhang, Junpeng
    Zhang, Di
    Cheng, Maosheng
    Lin, Bin
    Liu, Yongxiang
    [J]. CHEMICAL COMMUNICATIONS, 2022, 58 (18) : 3051 - 3054
  • [5] Quantum Mechanical Investigations of Organocatalysis: Mechanisms, Reactivities, and Selectivities
    Cheong, Paul Ha-Yeon
    Legault, Claude Y.
    Um, Joann M.
    Celebi-Oelcuem, Nihan
    Houk, K. N.
    [J]. CHEMICAL REVIEWS, 2011, 111 (08) : 5042 - 5137
  • [6] Computational chemistry strategies in natural product synthesis
    Elkin, Masha
    Newhouse, Timothy R.
    [J]. CHEMICAL SOCIETY REVIEWS, 2018, 47 (21) : 7830 - 7844
  • [7] Monoterpene indole alkaloids as leads for targeting multidrug resistant cancer cells from the African medicinal plant Tabernaemontana elegans
    Ferreira, Maria-Jose U.
    Paterna, Angela
    [J]. PHYTOCHEMISTRY REVIEWS, 2019, 18 (04) : 971 - 987
  • [8] Gold Catalysis: A Reflection on Where We are Now
    Freakley, Simon J.
    He, Qian
    Kiely, Christopher J.
    Hutchings, Graham J.
    [J]. CATALYSIS LETTERS, 2015, 145 (01) : 71 - 79
  • [9] Design and Application of a Screening Set for Monophosphine Ligands in Cross-Coupling
    Gensch, Tobias
    Smith, Sleight R.
    Colacot, Thomas J.
    Timsina, Yam N.
    Xu, Guolin
    Glasspoole, Ben W.
    Sigman, Matthew S.
    [J]. ACS CATALYSIS, 2022, 12 (13) : 7773 - 7780
  • [10] Harper KC, 2012, NAT CHEM, V4, P366, DOI [10.1038/NCHEM.1297, 10.1038/nchem.1297]