Formal [4+2] cycloaddition of 3-phenylcyclobutanones with nitriles

被引:18
|
作者
Igarashi, Emiko [1 ]
Sakamoto, Kenta [1 ]
Yoshimura, Tomoyuki [1 ]
Matsuo, Jun-ichi [1 ]
机构
[1] Kanazawa Univ, Grad Sch Med Sci, Div Pharmaceut Sci, Kanazawa, Ishikawa 9201192, Japan
关键词
Cyclobutanone; Nitrile; Dihydropyridone; Lewis acid; Cycloaddition; ACCEPTOR CYCLOPROPANES; ASYMMETRIC-SYNTHESIS; GRIGNARD-REAGENTS; DONOR; RING; 2-ARYL-N-TOSYLAZETIDINES; CLEAVAGE;
D O I
10.1016/j.tetlet.2018.11.040
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various 3-phenylcyclobutanones reacted with aliphatic and aromatic nitriles in the presence of Me3SiOTf to afford dihydropyridones by formal [4+2] cycloaddition. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:13 / 15
页数:3
相关论文
共 50 条
  • [21] Palladium-Catalyzed Decarboxylative Formal (4+2) Cycloaddition of Vinyl Benzoxazinanones with 3-Nitroindoles
    Bird, Melissa J.
    Wales, Steven M.
    Richardson, Christopher
    Hyland, Christopher J. T.
    SYNLETT, 2020, 31 (09) : 916 - 924
  • [22] Formal [4+2] cycloaddition of cyclobutanones bearing alkyne-cobalt complex at their 3-positions
    Kawano, Mizuki
    Kiuchi, Takaaki
    Matsuo, Jun-ichi
    Ishibashi, Hiroyuki
    TETRAHEDRON LETTERS, 2012, 53 (04) : 432 - 434
  • [23] 2-aryl-N-tosylazetidines as formal 1,4-dipoles for [4+2] cycloaddition reactions with nitriles:: An easy access to the tetrahydropyrimidine derivatives
    Prasad, BAB
    Bisai, A
    Singh, VK
    ORGANIC LETTERS, 2004, 6 (26) : 4829 - 4831
  • [24] Nickel-Catalyzed Dehydrogenative [4+2] Cycloaddition of 1,3-Dienes with Nitriles
    Ohashi, Masato
    Takeda, Ippei
    Ikawa, Masashi
    Ogoshi, Sensuke
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (45) : 18018 - 18021
  • [25] A formal [4+2] cycloaddition of sulfur-containing alkylidene heterocycles with allenic compounds
    Docekal, Vojtech
    Formanek, Bedrich
    Cisarova, Ivana
    Vesely, Jan
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (18) : 3259 - 3263
  • [26] Stereoselective synthesis of tetrahydropyrans via formal [4+2]-cycloaddition: A comparison of allylsilane and crotylsilane
    Angle, SR
    Belanger, DS
    El-Said, NA
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (22): : 7699 - 7705
  • [27] Development of Formal [4+2] Cycloaddition Reactions by Using Cyclobutanones Bearing Donor Substituents at their 3-Positions
    Matsuo, Junichi
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2016, 74 (06) : 582 - 587
  • [28] Cinchona alkaloid-catalyzed formal [4+2] cycloaddition of allenoates and a, β-unsaturated trifluoromethylketones
    Kasten, Kevin
    Smith, Andrew
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [29] Ytterbium-catalyzed formal [4+2] cycloaddition: Synthesis of chalcogen-quinolines 3-unsubstituted
    de Oliveira, Isadora M.
    Darbem, Mariana P.
    Esteves, C. Henrique A.
    Pimenta, Daniel C.
    Zukerman-Schpector, Julio
    Stefani, Helio A.
    Manarin, Flavia
    TETRAHEDRON LETTERS, 2018, 59 (44) : 3907 - 3911
  • [30] Synthesis of Densely Substituted Pyridine Derivatives from 1-Methyl-1,3-(ar)enynes and Nitriles by a Formal [4+2] Cycloaddition Reaction
    He, Dandan
    Wang, Bowen
    Duan, Kanghui
    Zhou, Yang
    Li, Meng
    Jiang, Huanfeng
    Wu, Wanqing
    ORGANIC LETTERS, 2022, 24 (06) : 1292 - 1297