N-Sulfonyl acetylketenimine as a highly reactive intermediate for the synthesis of N-sulfonyl amidines

被引：40
|
作者：
Yang, Weiguang [1 ]
Huang, Dayun [1 ]
Zeng, Xiaobao [1 ]
Luo, Dongping [1 ]
Wang, Xinyan [1 ]
Hu, Yuefei [1 ]
机构：
[1] Tsinghua Univ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Beijing 100084, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 59期
基金：
中国国家自然科学基金;
关键词：
AZIDE-ALKYNE CYCLOADDITION; ONE-POT SYNTHESIS; COPPER-CATALYZED REACTION; LIGAND-FREE; CONTROLLING SELECTIVITY; CYCLIC AMIDINES; MILD CONDITIONS; DERIVATIVES; CHEMISTRY; DESIGN;
D O I：
10.1039/c8cc04699a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A highly reactive intermediate N-sulfonyl acetylketenimine was generated from a 3-butyn-2-one participating CuAAC/ring-opening method. Its high reactivity due to bearing two EWGs allowed us to offer the first example of a reaction between ketenimine and amide to synthesize N-sulfonyl amidines efficiently.
引用
收藏
页码：8222 / 8225
页数：4
相关论文
共 50 条
  • [41] Interception of amide ylides with sulfonamides: synthesis of (E)-N-sulfonyl amidines catalyzed by Zn(OTf)2
    Chen, Jijun
    Long, Wenhao
    Fang, Shangwen
    Yang, Yonggang
    Wan, Xiaobing
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (99) : 13256 - 13259
  • [42] Investigation of UV Light-Promoted Synthesis of α-Sulfonyl Amides from N-Sulfonyl Ynamides
    Galibert-Guijarro, Aurelien
    Tronc, Jeremy
    Mouysset, Dominique
    Siri, Didier
    Gastaldi, Stephane
    Bertrand, Michele P.
    Feray, Laurence
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (13): : 9695 - 9699
  • [43] Synthesis of Chiral N-Sulfonyl and N-Phosphinoyl -Halo Aldimine Precursors
    Stanton, Gretchen R.
    Goellue, Mehmet
    Platoff, Rebecca M.
    Rich, Corinne E.
    Carroll, Patrick J.
    Walsh, Patrick J.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (04) : 757 - 764
  • [44] An Easy One-Pot Procedure for the Synthesis of N-Sulfonyl Phosphorous Ylides and Sulfonyl Iminophosphoranes
    Ahmad Shaabani
    Abbas Rahmati
    Soheila Naderi
    [J]. Monatshefte für Chemie - Chemical Monthly, 2007, 138 : 553 - 557
  • [45] An easy one-pot procedure for the synthesis of N-sulfonyl phosphorous ylides and sulfonyl iminophosphoranes
    Shaabani, Ahmad
    Rahmati, Abbas
    Naderi, Soheila
    [J]. MONATSHEFTE FUR CHEMIE, 2007, 138 (06): : 553 - 557
  • [46] Two-step synthesis of N-sulfonyl aziridines from epoxides
    Huang, Jianhui
    O'Brien, Peter
    [J]. Synthesis, 2006, (03): : 425 - 434
  • [47] Synthesis of novel N-sulfonyl monocyclic β-lactams as potential antibacterial agents
    Jarrahpour, A
    Zarei, M
    [J]. MOLECULES, 2006, 11 (01): : 49 - 58
  • [48] Fluoroalkyl N-sulfonyl hydrazones: An efficient reagent for the synthesis of fluoroalkylated compounds
    Paramasivam Sivaguru
    Xihe Bi
    [J]. Science China Chemistry, 2021, (10) : 1614 - 1629
  • [49] A general method for the preparation of N-sulfonyl aldimines and ketimines
    Ruano, JLG
    Alemán, J
    Cid, MB
    Parra, A
    [J]. ORGANIC LETTERS, 2005, 7 (02) : 179 - 182
  • [50] SUBSTITUTION OF N-SULFONYL GROUPS UNDER ELECTROPHILIC ATTACK
    MARKOV, VI
    DMITRIKOVA, LV
    DUBINA, VL
    BURMISTROV, KS
    [J]. ZHURNAL ORGANICHESKOI KHIMII, 1988, 24 (11): : 2463 - 2464
12345