Lewis acid catalyzed condensation of 2-aminohetarene N-oxides with N,N-dimethylformamide dimethyl acetal

被引:0
|
作者
Sergey А. Karalash
Dmitry M. Bystrov
Ivan V. Ananyev
Leonid L. Fershtat
机构
[1] N. D. Zelinsky Institute of Organic Chemistry,
[2] Russian Academy of Sciences,undefined
[3] Lomonosov Moscow State University,undefined
[4] A. N. Nesmeyanov Institute of Organoelement Compounds,undefined
[5] Russian Academy of Sciences,undefined
来源
关键词
azines; heterocyclic ; -oxides; Lewis acids; nitrogen-containing heterocycles; pyridines; condensation; protective groups;
D O I
暂无
中图分类号
学科分类号
摘要
A method for the introduction of the N,N-dimethylformamidine protective group in a series of six-membered 2-aminohetarene N-oxides was developed. It was shown that 2-amino derivatives of N-oxides of various six-membered heterocycles (pyridines, pyrimidines, pyrazines, tetrazines) successfully enter the reaction. The stability of the N,N-dimethylformamidine protecting group in 2-aminohetarene N-oxides was found to depend on the type of reaction medium.
引用
收藏
页码:1130 / 1136
页数:6
相关论文
共 50 条
  • [21] 2,5-Dibenzoylterephthalic acid N,N-dimethylformamide disolvate
    Liu, Shan
    Wu, Wen-Yuan
    Wen, Fan
    Liu, Rui
    Zhu, Hong-Jun
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O515 - O516
  • [22] N-METHYLATION OF HETEROCYCLES WITH DIMETHYLFORMAMIDE DIMETHYL ACETAL
    MIDDLETON, RW
    MONNEY, H
    PARRICK, J
    [J]. SYNTHESIS-STUTTGART, 1984, (09): : 740 - 743
  • [23] Sulfation of Xylan with Sulfamic Acid in N,N-Dimethylformamide
    Levdansky, V. A.
    Kondrasenko, A. A.
    Levdansky, A. V.
    Kuznetsov, B. N.
    [J]. RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2019, 45 (07) : 882 - 887
  • [24] Sulfation of Xylan with Sulfamic Acid in N,N-Dimethylformamide
    V. A. Levdansky
    A. A. Kondrasenko
    A. V. Levdansky
    B. N. Kuznetsov
    [J]. Russian Journal of Bioorganic Chemistry, 2019, 45 : 882 - 887
  • [25] Pd-Catalyzed N-Formylation of Amines with N, N-Dimethylformamide
    Li, Chun
    Wang, Mengna
    Lu, Xunhua
    Yang, Yuanyong
    Zhang, Lin
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (04) : 1109 - 1115
  • [26] Solubility of Tobramycin in Methanol, Ethanol, Dimethyl Sulfoxide, and N,N-Dimethylformamide
    Chen, Yi
    Zhu, Liang
    Gao, Yi-Ying
    Wang, Jing-Kang
    [J]. JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2009, 54 (04): : 1403 - 1404
  • [27] METHYLATION OF HETEROCYCLIC-COMPOUNDS CONTAINING NH, SH AND-OR OH GROUPS BY MEANS OF N,N-DIMETHYLFORMAMIDE DIMETHYL ACETAL
    STANOVNIK, B
    TISLER, M
    HRIBAR, A
    BARLIN, GB
    BROWN, DJ
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (08) : 1729 - 1738
  • [28] Explosion Hazards of Sodium Hydride in Dimethyl Sulfoxide, N,N-Dimethylformamide, and N,N-Dimethylacetamide
    Yang, Qiang
    Sheng, Min
    Henkelis, James J.
    Tu, Siyu
    Wiensch, Eric
    Zhang, Honglu
    Zhang, Yiqun
    Tucker, Craig
    Ejeh, David E.
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (10) : 2210 - 2217
  • [29] NOVEL CONVERSION OF N,N-DIMETHYLFORMAMIDE DIMETHYL ACETAL TO TETRAMETHYLAMMONIUM SALTS BY ITS REACTION WITH 5-METHYL-4-ISOXAZOLECARBOXYLIC ACID-DERIVATIVES
    SINGH, B
    HLAVAC, AG
    [J]. CHEMISTRY LETTERS, 1991, (01) : 41 - 42
  • [30] SYNTHESIS OF N,N-DIMETHYLFORMAMIDE AND N,N-DIMETHYLACETAMIDE ADDUCTS WITH XYLOTRIHYDROXYGLUTARIC ACID
    REPIN, AG
    MAKAROVZ.YY
    [J]. ZHURNAL OBSHCHEI KHIMII, 1973, 43 (09): : 2092 - 2093