Synthesis and Alkylation of Diethyl 6-Aryl-2-Oxo-1,2,3,6-Tetrahydropyrimidine-4,5-Dicarboxylates

被引:0
作者
M. A. Kolosov
M. J. K. Al-Ogaili
V. S. Parkhomenko
V. D. Orlov
机构
[1] V. N. Karazin Kharkiv National University,
来源
Chemistry of Heterocyclic Compounds | 2014年 / 49卷
关键词
diethyl 2-oxo-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates; oxalacetic ester; alkylation; Biginelli reaction;
D O I
暂无
中图分类号
学科分类号
摘要
We have demonstrated the preparation of diethyl 6-aryl-2-oxo-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates by reaction of urea, oxalacetic ester, and aromatic aldehydes with substituents of various electronic properties. Alkylation of the obtained compounds in the alkyl halogenide–KOH/Н2О–MeCN system resulted in mixtures of N-alkyl derivatives, which can be separated by column chromatography. Longer reaction time led selectively to 1,3-dialkylation products.
引用
收藏
页码:1484 / 1489
页数:5
相关论文
共 50 条
  • [31] Reaction of ethyl 4-aryl-6-bromomethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates with N-methylmorpholinium 3-cyano-1,4-dihydro- and 3-cyano-1,4,5,6-tetrahydropyridine-2-thiolates
    Dotsenko, V. V.
    Lebedeva, I. A.
    Krivokolysko, S. G.
    Povstyanoi, M. V.
    Povstyanoi, V. M.
    Kostyrko, E. O.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (03) : 462 - 469
  • [32] A GREENER CHEMISTRY APPROACH FOR SYNTHESIS OF 4-(4-HYDROXYPHENYL)-6-METHYL- 2-OXO-1,2,3,4 TETRAHYDROPYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER
    Jagwani, D.
    Joshi, P.
    INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES AND RESEARCH, 2015, 6 (02): : 783 - 790
  • [33] Synthesis and alkylation of 4-(2-chlorophenyl)-3-cyano-6-hydroxy-5- (2-thienoyl)-6-trifluoromethylpiperidin-2-thione
    Krivokolysko S.G.
    Dyachenko V.D.
    Rusanov E.B.
    Litvinov V.P.
    Chemistry of Heterocyclic Compounds, 2001, 37 (8) : 987 - 992
  • [34] Synthesis and Structure of Methyl 6-Aryl-5-aroyl-4-hydroxy2-oxo(thioxo)hexahydropyrimidine-4-carboxylates
    Gein, V. L.
    Zamaraeva, T. M.
    Gorgopina, E. V.
    Dmitriev, M. V.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2022, 92 (10) : 1894 - 1898
  • [35] Synthesis and Structure of Methyl 6-Aryl-5-aroyl-4-hydroxy2-oxo(thioxo)hexahydropyrimidine-4-carboxylates
    V. L. Gein
    T. M. Zamaraeva
    E. V. Gorgopina
    M.V. Dmitriev
    Russian Journal of General Chemistry, 2022, 92 : 1894 - 1898
  • [36] Multicomponent synthesis and anticancer activity studies of novel 6-(Trifluoromethyl)-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylate derivatives
    Valeru, Anil
    Luo, Zhi-Bin
    Khan, Imran
    Liu, Bin
    Sngepu, Bhavanarushi
    Godumagadda, Narender Reddy
    Xu, Yin
    Xie, Jimin
    SYNTHETIC COMMUNICATIONS, 2018, 48 (17) : 2226 - 2231
  • [37] Ultrasound-Assisted Synthesis of 6-Methyl-1,2,3,4-tetrahydro-N-aryl-2-oxo/thio-4-arylpyrimidine-5-carboxamides Catalyzed by Uranyl Nitrate Hexahydrate
    Venkatesan, K.
    Satyanarayana, V. S. V.
    Sivakumar, A.
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2014, 61 (06) : 624 - 630
  • [38] Synthesis and properties of (6-methyl-2-oxo-4-thioxo-1,2,3,4-tetrahydro-3- pyrimidinyl)acetic acid methyl ester
    Jakubkiene V.
    Paulauskaite R.
    Vainilavicius P.
    Chemistry of Heterocyclic Compounds, 2007, 43 (4) : 485 - 489
  • [39] Ethyl 6-Methyl-2-oxo-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-1,2,3,4-tetrahydropyrimidine-5-carboxylate
    Goncalves, Itamar Luis
    de Azambuja, Gabriel Oliveira
    Davi, Leonardo
    Goncalves, Guilherme Arrache
    Kagami, Luciano Porto
    das Neves, Gustavo Machado
    Silveira, Joao Pedro
    Santos Canto, Romulo Faria
    Eifler-Lima, Vera Lucia
    MOLBANK, 2019, 2019 (03)
  • [40] Synthesis of 5-alkyl-1,3-bis[2-hydroxy-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)propyl]-6-methyl-1,2,3,4-tetrahydropyrimidine-2,4-diones
    Krivonogov, VP
    Kozlova, GG
    Belaya, EA
    Sivkova, GA
    Spirikhin, LV
    Abdrakhmanov, IB
    Plechev, VV
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (03) : 417 - 420