A combinatorially convenient version of synthesis of 5-substituted oxazole-4-carboxylic acid ethyl esters

被引:0
|
作者
V. M. Tormyshev
T. V. Mikhalina
O. Yu. Rogozhnikova
T. I. Troitskaya
D. V. Trukhin
机构
[1] Russian Academy of Sciences,Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division
来源
关键词
Sodium; Chloride; Ester; Ethyl; Benzene;
D O I
暂无
中图分类号
学科分类号
摘要
Reaction of ethyl isocyanoacetic acid with sodium hydride in anhydrous benzene, followed by treatment with carboxylic acid chlorides or N-(acyloxy)pyrrolidine-2,5-diones, gives 5-substituted oxazole-4-carboxylic acid esters. The procedure is applicable to derivatives of various carboxylic acids, including saturated aliphatic, α,β-unsaturated, alicyclic, aromatic, heterocyclic, and N-Boc-protected amino acids.
引用
收藏
页码:1031 / 1035
页数:4
相关论文
共 50 条
  • [1] A combinatorially convenient version of synthesis of 5-substituted oxazole-4-carboxylic acid ethyl esters
    Tormyshev, V. M.
    Mikhalina, T. V.
    Rogozhnikova, O. Yu.
    Troitskaya, T. I.
    Trukhin, D. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 42 (07) : 1031 - 1035
  • [2] SYNTHESES OF 5-SUBSTITUTED OXAZOLE-4-CARBOXYLIC ACID-DERIVATIVES WITH INHIBITORY ACTIVITY ON BLOOD-PLATELET AGGREGATION
    OZAKI, Y
    MAEDA, S
    IWASAKI, T
    MATSUMOTO, K
    ODAWARA, A
    SASAKI, Y
    MORITA, T
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1983, 31 (12) : 4417 - 4424
  • [3] Studies towards a biomimetic synthesis of α-cyclopiazonic acid:: synthesis of 5-substituted isoxazole-4-carboxylic esters
    Moorthie, Vijayalakshmi A.
    McGarrigle, Eoghan M.
    Stenson, Rachel
    Aggarwal, Varinder K.
    ARKIVOC, 2007, : 139 - 151
  • [4] Design, Synthesis, Docking Studies and Antimicrobial Activity of 5-Substituted 4-Phenyl-2-(Phenylamino) Thiophene-3-Carboxylic Acid Ethyl Esters
    Asiri, Yahya, I
    Alsayari, Abdulrhman
    Bin Muhsinah, Abdullatif
    Venkatesan, Kumar
    Al-Ghorbani, Mohammed
    Mabkhot, Yahia N.
    POLYCYCLIC AROMATIC COMPOUNDS, 2023, 43 (03) : 1929 - 1940
  • [5] Facile Synthesis of 4-Substituted-2-quinolinone-3-carboxylic Acid Ethyl Esters
    Zhang, Lijuan
    Luo, Yu
    Yu, Shanbao
    Lu, Wei
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (05) : 1254 - 1256
  • [6] A SIMPLE AND CONVENIENT SYNTHESIS OF 5-SUBSTITUTED BENZOXAZOLES
    KUNZ, KR
    TAYLOR, EW
    HUTTON, HM
    BLACKBURN, BJ
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1990, 22 (05) : 613 - 618
  • [7] ALPHA,BETA-UNSATURATED CARBOXYLIC-ACID DERIVATIVES .12. CONVENIENT SYNTHESIS OF OXAZOLE-4-CARBOXYLIC AND 3,3-DIBROMO-2,2-DIAMINO ACIDS
    SHIN, C
    SATO, Y
    SUGIYAMA, H
    NANJO, K
    YOSHIMURA, J
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (07) : 1788 - 1792
  • [8] Synthesis of Isoxazole- and Oxazole-4-carboxylic Acids Derivatives by Controlled Isoxazole-Azirine-Isoxazole/Oxazole Isomerization
    Serebryannikova, Anna V.
    Galenko, Ekaterina E.
    Novikov, Mikhail S.
    Khlebnikov, Alexander F.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (23): : 15567 - 15577
  • [9] Convenient synthesis of novel 5-substituted 3-methylisoxazole-4-sulfonamides
    Filimonov, Sergey I.
    Korsakov, Mikhail K.
    Kravchenko, Dmitry V.
    Dorogov, Mikhail V.
    Tkachenko, Sergey E.
    Ivachtchenko, Alexandre V.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (03) : 663 - 671
  • [10] A convenient oxazole C-2 protecting group: The synthesis of 4-and 5-substituted oxazoles via metalation of 2-triisopropylsilyloxazoles
    Miller, RA
    Smith, RM
    Marcune, B
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (22): : 9074 - 9076