Phosphine-mediated annulation of N-protected imines with DEAD

被引：11
|
作者：
Lian, Zhong [1 ]
Guan, Xiao-Yang [1 ]
Shi, Min [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON | 2011年 / 67卷 / 11期
基金：
中国国家自然科学基金;
关键词：
Triphenylphosphine; N-Protected imine; DEAD; Annulations; CATALYZED 4+2 ANNULATION; BAYLIS-HILLMAN; ALLYLIC COMPOUNDS; ALLENES; TRIPHENYLPHOSPHINE; 2,3-BUTADIENOATE; CYCLOADDITION; CYCLOPENTENES; TOSYLIMINES; ZWITTERIONS;
D O I：
10.1016/j.tet.2011.01.072
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In the presence of triphenylphosphine, the reactions of N-protected imines or their precursors with DEAD proceeded smoothly to give the corresponding functionalized 1H-1,2,4-triazole-1,4(5H)-di-carboxylate derivatives in good to high yields under mild conditions. A plausible mechanism has been proposed on the basis of the control experiments. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2018 / 2024
页数：7
相关论文
共 50 条
  • [1] Asymmetric Aza-Morita-Baylis-Hillman Reactions of Alkyl Vinyl Ketones with N-Protected Imines or In Situ Generated N-Protected Imines
    Guan, Xiao-Yang
    Wei, Yin
    Shi, Min
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (21) : 4098 - 4105
  • [2] Synthesis of azulenophthalimides by phosphine-mediated annulation of 1,2-diformylazulenes with maleimides
    Shoji, Taku
    Araki, Takanori
    Iida, Nanami
    Miura, Kota
    Ohta, Akira
    Sekiguchi, Ryuta
    Ito, Shunji
    Okujima, Tetsuo
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (02) : 195 - 204
  • [3] A Direct Phosphine-Mediated Synthesis of Pyrroles from Acid Chlorides and α,β-Unsaturated Imines
    Lu, Yingdong
    Arndtsen, Bruce A.
    ORGANIC LETTERS, 2009, 11 (06) : 1369 - 1372
  • [4] Enantioselective addition of oxazolones to N-protected imines catalysed by chiral thioureas
    Zabka, Matej
    Malastova, Andrea
    Sebesta, Radovan
    RSC ADVANCES, 2015, 5 (17): : 12890 - 12893
  • [5] Phosphine-Mediated Sequential Annulation Reaction: Access to Functionalized Benzofurans and 4,5-Dihydrobenzofurans
    Liang, Ling
    Dong, Xuelin
    Huang, You
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (33) : 7882 - 7886
  • [6] Phosphine-Mediated Sequential [2+4]/[2+3] Annulation to Construct Pyrroloquinolines
    Lin, Junhui
    Zhu, Yannan
    Cai, Wei
    Huang, You
    ORGANIC LETTERS, 2022, 24 (08) : 1593 - 1597
  • [7] Phosphine-mediated dehalogenation reactions of trichloro(N-silyl)phosphoranimines
    Huynh, Keith
    Rivard, Eric
    LeBlanc, Wesley
    Blackstone, Vivienne
    Lough, Alan J.
    Manners, Ian
    INORGANIC CHEMISTRY, 2006, 45 (19) : 7922 - 7928
  • [8] Recent topics of phosphine-mediated reactions
    Karanam, Praneeth
    Reddy, Ganapuram Madhusudhan
    Koppolu, Srinivasa Rao
    Lin, Wenwei
    TETRAHEDRON LETTERS, 2018, 59 (02) : 59 - 76
  • [9] Chiral phosphine-mediated intramolecular [3+2] annulation: enhanced enantioselectivity by achiral Bronsted acid
    Yao, Weijun
    Yu, Zhaoyuan
    Wen, Shan
    Ni, Huanzhen
    Ullah, Nisar
    Lan, Yu
    Lu, Yixin
    CHEMICAL SCIENCE, 2017, 8 (07) : 5196 - 5200
  • [10] Phosphine-Mediated Bioconjugation of the 3'-End of RNA
    Kitoun, Camelia
    Fonvielle, Matthieu
    Sakkas, Nicolas
    Lefresne, Manon
    Djago, Fabiola
    Remaury, Quentin Blancart
    Poinot, Pauline
    Arthur, Michel
    Etheve-Quelquejeu, Melanie
    Iannazzo, Laura
    ORGANIC LETTERS, 2020, 22 (20) : 8034 - 8038
12345