Nucleophilic Addition Reactions of Nitriles to Nitrones under Mild Silylation Conditions

被引：9
|
作者：
Yoshimura, Fumihiko [1 ]
Abe, Taiki [2 ]
Tanino, Keiji [1 ]
机构：
[1] Hokkaido Univ, Dept Chem, Fac Sci, Sapporo, Hokkaido 0600810, Japan
[2] Hokkaido Univ, Grad Sch Chem Sci & Engn, Sapporo, Hokkaido 0600810, Japan
来源：
SYNLETT | 2014年 / 25卷 / 13期
关键词：
nucleophilic addition; nitriles; nitrones; amines; hydroxylamine; TRIMETHYLSILYL; ALKYLATION; ANALOGS;
D O I：
10.1055/s-0034-1378274
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In the presence of triethylsilyl trifluoromethanesulfonate and triethylamine, aliphatic nitriles undergo addition reactions with aldonitrones under non-basic, mild conditions, providing O-triethylsilyl ethers of beta-N-hydroxyamino nitriles with high yield. The reaction appears to proceed through formation of an N-silyl ketene imine in situ followed by a Mannich-type reaction.
引用
收藏
页码：1863 / 1868
页数：6
相关论文
共 50 条
  • [1] Deoxygenation of triglycerides by silylation under exceptionally mild conditions
    Gale, Cody B.
    Brook, Michael A.
    GREEN CHEMISTRY, 2018, 20 (16) : 3717 - 3721
  • [2] Organic reactions in water: Transformation of aldehydes to nitriles using NBS under mild conditions
    Bandgar, BP
    Makone, SS
    SYNTHETIC COMMUNICATIONS, 2006, 36 (10) : 1347 - 1352
  • [3] Understanding the high diastereofacial discrimination in nucleophilic additions to nitrones: the first ab initio study on the nucleophilic addition reactions of chiral nitrones with Grignard reagents
    Merino, P
    Tejero, T
    TETRAHEDRON, 2001, 57 (38) : 8125 - 8128
  • [4] Nucleophilic Addition to Nitrones Using a Flow Microreactor
    Arakawa, Yukihiro
    Ueta, Shun
    Okamoto, Takuma
    Minagawa, Keiji
    Imada, Yasushi
    SYNLETT, 2020, 31 (09) : 866 - 870
  • [5] Unsaturated polyesters prepared under mild reaction conditions by aliphatic nucleophilic substitution reactions
    Parthiban, Anbanandam
    Rao, T. R. Babu
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [6] Conversion of aldoximes into nitriles and amides under mild conditions
    Tambara, Koujiro
    Pantos, G. Dan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (15) : 2466 - 2472
  • [7] SELECTIVE HYDROLYSIS OF NITRILES UNDER MILD CONDITIONS BY AN ENZYME
    COHEN, MA
    SAWDEN, J
    TURNER, NJ
    TETRAHEDRON LETTERS, 1990, 31 (49) : 7223 - 7226
  • [8] 1,3-DIPOLAR ADDITION OF OXIMES TO OLEFINS - CONVERSION OF ALDOXIMES TO NITRILES UNDER MILD CONDITIONS
    DALGARD, NKA
    LARSEN, KE
    TORSSELL, KBG
    ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1984, 38 (05): : 423 - 432
  • [9] Reactions of cyclic α-methoxy nitrones with nucleophilic reagents
    Grigor'ev, IA
    Bakunova, SM
    Kirilyuk, IA
    RUSSIAN CHEMICAL BULLETIN, 2000, 49 (12) : 2031 - 2036
  • [10] Reactions of cyclic α-methoxy nitrones with nucleophilic reagents
    I. A. Grigor'ev
    S. M. Bakunova
    I. A. Kirilyuk
    Russian Chemical Bulletin, 2000, 49 : 2031 - 2036
12345