Convenient synthesis of N1-substituted orotic acid derivatives

被引:7
|
作者
Bowler, Jeannette T. [1 ]
Clausen, Caitlin R. [1 ]
Blackburn, Daniel J. [1 ]
Wu, Weiming [1 ]
机构
[1] San Francisco State Univ, Dept Chem & Biochem, San Francisco, CA 94132 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
Orotic acid; Orotidine; Synthesis; Maleimide; Bromomaleimide; Dibromosuccinimide; 1,3-DIMETHYLOROTIC ACID; OROTIDINE-5'-MONOPHOSPHATE DECARBOXYLASE; MECHANISTIC IMPLICATIONS; PROFICIENT ENZYME; CARBANIONS; MALEIMIDES; STABILITY; ANALOGS; URACIL; MODEL;
D O I
10.1016/j.tetlet.2014.10.005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient and efficient method for the synthesis of N1-substituted orotic acid derivatives is reported. The synthetic route utilizes substituted maleimide as synthetic intermediate and takes only four simple steps from readily available starting materials. As a result, orotic acid derivatives with various alkyl and aromatic groups at N1 can be readily synthesized. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6465 / 6466
页数:2
相关论文
共 50 条
  • [21] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF SOME N(1)-SUBSTITUTED OROTIC ACIDS
    SHOPOVA, M
    TABAKOVA, S
    TAXIROV, S
    GOLOVINSKY, E
    PHARMAZIE, 1993, 48 (11): : 861 - 862
  • [22] N1-SUBSTITUTED 6-THIOPURINE NUCLEOSIDES
    RATSEP, PC
    MISHRA, NC
    BROOM, AD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 201 : 27 - CARB
  • [23] Cycloalkyl substituted N-nitrourea derivatives: a convenient synthesis and biological evaluation
    Bai, Zhongyuan
    Wei, Zengjun
    Wang, Yunchun
    Xu, Shengzhen
    Li, Xuegang
    Chen, Changshui
    Cao, Xiufang
    RESEARCH ON CHEMICAL INTERMEDIATES, 2011, 37 (08) : 859 - 868
  • [24] Cycloalkyl substituted N-nitrourea derivatives: a convenient synthesis and biological evaluation
    Zhongyuan Bai
    Zengjun Wei
    Yunchun Wang
    Shengzhen Xu
    Xuegang Li
    Changshui Chen
    Xiufang Cao
    Research on Chemical Intermediates, 2011, 37 : 859 - 868
  • [25] CONVENIENT SYNTHESIS OF HIGHLY SUBSTITUTED IMIDAZOLE DERIVATIVES
    Wong, Lai Chun
    Gehre, Alexander
    Stanforth, Stephen P.
    Tarbit, Brian
    SYNTHETIC COMMUNICATIONS, 2013, 43 (01) : 80 - 84
  • [26] A CONVENIENT PROCEDURE FOR THE SYNTHESIS OF N-SUBSTITUTED-N-GLYCOLYL-1,2-AMINOETHANOL DERIVATIVES
    PLUMET, J
    LOPEZ, B
    DELVALLE, A
    SYNTHETIC COMMUNICATIONS, 1993, 23 (16) : 2235 - 2240
  • [27] A convenient synthesis of N1-substituted 3,4-dihydropyrimidin-2(1H)-ones by cyclocondensation of α-chlorobenzyl isocyanates with ethyl N-alkyl(aryl)-β-aminocrotonates
    Sukach, VA
    Bol'but, AV
    Sinitsa, AD
    Vovk, MV
    SYNLETT, 2006, (03) : 375 - 378
  • [28] A convenient synthesis of novel N′-tert-butyl-N′-substituted benzoyl-N-(substituted phenyl)aminocarbonylhydrazines and their derivatives
    Wang, QM
    Huang, RQ
    SYNTHETIC COMMUNICATIONS, 2004, 34 (02) : 255 - 264
  • [29] TAUTOMERISM OF N1-SUBSTITUTED PYRAZOLIN-5-THIONES
    MAQUESTIAU, A
    VANHAVERBEKE, Y
    VANOVERVELT, JC
    BULLETIN DES SOCIETES CHIMIQUES BELGES, 1977, 86 (12): : 949 - 959