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
  • [1] Lewis acid catalyzed condensation of 2-aminohetarene N-oxides with N,N-dimethylformamide dimethyl acetal
    Karalash, Sergey A.
    Bystrov, Dmitry M.
    Ananyev, Ivan V.
    Fershtat, Leonid L.
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (11) : 1130 - 1136
  • [2] N,N-Dimethylformamide dimethyl acetal
    Kidjemet, D
    [J]. SYNLETT, 2002, (10) : 1741 - 1742
  • [3] Tandem Condensation/Rearrangement Reaction of 2-Aminohetarene N-Oxides for the Synthesis of Hetaryl Carbamates
    Bystrov, Dmitry M.
    Zhilin, Egor S.
    Fershtat, Leonid L.
    Romanova, Anna A.
    Ananyev, Ivan V.
    Makhova, Nina N.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (16) : 3157 - 3163
  • [4] ACID-BASE EQUILIBRIA OF SUBSTITUTED PYRIDINE N-OXIDES IN N,N-DIMETHYLFORMAMIDE AND DIMETHYL-SULFOXIDE
    CHMURZYNSKI, L
    WARNKE, Z
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1993, 46 (02) : 185 - 194
  • [5] REACTION OF N,N-DIMETHYLFORMAMIDE DIMETHYL ACETAL WITH AMINO-SUGARS
    STEFANSKA, B
    FALKOWSKI, L
    [J]. POLISH JOURNAL OF CHEMISTRY, 1982, 56 (4-6) : 855 - 857
  • [6] NAPHTHALENES AND BIPHENYLS VIA A NOVEL REACTION OF N,N-DIMETHYLFORMAMIDE DIMETHYL ACETAL
    ABDULLA, RF
    FUHR, KH
    GAJEWSKI, RP
    SUHR, RG
    TAYLOR, HM
    UNGER, PL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (09): : 1724 - 1725
  • [7] CONVENIENT CYCLIZATION OF ORTHO-DIFUNCTIONAL HETEROCYCLES WITH N,N-DIMETHYLFORMAMIDE DIMETHYL ACETAL
    STANOVNI.B
    TISLER, M
    [J]. SYNTHESIS-STUTTGART, 1974, (02): : 120 - 122
  • [8] PREPARATION OF OXAZOLINE N-OXIDES AND IMIDATE N-OXIDES BY AMIDE ACETAL CONDENSATION AND THEIR [3 + 2] CYCLO-ADDITION REACTIONS
    ASHBURN, SP
    COATES, RM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (17): : 3076 - 3081
  • [9] SYNTHESIS OF SUBSTITUTED NICOTINAMIDES FROM ENAMINES DERIVED FROM N,N-DIMETHYLFORMAMIDE DIMETHYL ACETAL
    ABUSHANAB, FA
    ALY, FM
    WAKEFIELD, BJ
    [J]. SYNTHESIS-STUTTGART, 1995, (08): : 923 - 925
  • [10] N,N-Dimethylformamide dimethyl acetal (DMFDMA): from derivatisation to C1 synthon
    Araujo, Natalie Ferreira
    Ferreira, Sabrina Baptista
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2024, 77 (06)