Synthesis and Structural Studies of Three Uracil Derivatives, Methyl 3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanate, Methyl 3-(5-Nitro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate and Ethyl 3-(5-Nitro-2,4-dioxo-3,4-dihydropyrimidin-1 (2H)-yl)propanoate

被引:0
|
作者
Liu, Wuqiang [1 ]
Feng, Xiaogang [1 ]
Tao, Yangyang [1 ]
Zhou, Zheng [1 ]
Wu, Guanghui [1 ]
Xiong, Jing [1 ]
机构
[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
关键词
Methyl 3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate; Methyl 3-(5-nitro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate; Ethyl 3-(5-nitro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate; Crystal structure; NMR spectra; FUNDAMENTAL FREQUENCIES; POTENT INHIBITORS; RAMAN-SPECTRA; IN-VITRO; 5-CHLOROURACIL; 5-FLUOROURACIL; MICHAEL; DESIGN; FTIR;
D O I
10.1007/s10870-014-0554-y
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
Three uracil derivatives of methyl 3-(2,4-dioxo-3,4- dihydropyrimidin-1(2H)-yl) propanoate (I), methyl 3-(5-nitro- 2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl) propanoate (II) and ethyl 3-(5-nitro-2,4-dioxo-3,4-dihydropyrimidin-1 (2H)-yl) propanoate (III) have been prepared through one pot synthesis and examined by X-ray crystallography, FT-IR and NMR spectroscopy. Compound I, C8H10N2O4, is monoclinic with space group P 21/c and cell constants a = 11.4437(12), b = 11.7980(13), c = 6.9496(7) angstrom, beta = 103.180(2)degrees, V = 913.57(17) angstrom(3), and Z = 4. Compound II, C8H9N3O6, crystallizes in the monoclinic P 21 space group with cell constants a = 8.0342(14), b = 5.7155(10), c = 11.572(2) angstrom, beta = 105.200(3)degrees, V = 512.79(16) angstrom(3), and Z = 2. Compound III, C9H11N3O6, is Orthorhombic with space group P 212121 and cell constants a = 5.7560(16), b = 8.032(2), c = 25.302(7) angstrom, beta = 90 degrees, V = 1169.8(6) angstrom(3), and Z = 4. The supramolecular architectures of the three compounds involve N-H center dot center dot center dot O hydrogen bond.
引用
收藏
页码:597 / 603
页数:7
相关论文
共 50 条
  • [1] Synthesis and Structural Studies of Three Uracil Derivatives, Methyl 3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanate, Methyl 3-(5-Nitro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate and Ethyl 3-(5-Nitro-2,4-dioxo-3,4-dihydropyrimidin-1 (2H)-yl)propanoate
    Wuqiang Liu
    Xiaogang Feng
    Yangyang Tao
    Zheng Zhou
    Guanghui Wu
    Jing Xiong
    Journal of Chemical Crystallography, 2014, 44 : 597 - 603
  • [2] Synthesis, Structural, and UV Studies of Two Uracil Derivatives, Methyl 3-(5-Fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate and Methyl 3-(5-Chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate
    Ting Yao
    Jicheng Yi
    Shuguang Zhou
    Jing Xiong
    Journal of Chemical Crystallography, 2013, 43 : 383 - 389
  • [3] Synthesis, Structural, and UV Studies of Two Uracil Derivatives, Methyl 3-(5-Fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate and Methyl 3-(5-Chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate
    Yao, Ting
    Yi, Jicheng
    Zhou, Shuguang
    Xiong, Jing
    JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2013, 43 (07) : 383 - 389
  • [4] N-functionalization of uracil derivatives:: synthesis of chiral 2-(3-methyl-5-nitro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)alkanoic acids and their methyl esters
    Gondela, A
    Walczak, K
    TETRAHEDRON-ASYMMETRY, 2005, 16 (12) : 2107 - 2112
  • [5] Crystal structure of 3-(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)yl) propionic acid methyl ester, C8H9BrN2O4
    Zhou, Shu-Guang
    Li, Ke-Rui
    Li, Da-Shuai
    Xu, Jing
    Xiong, Jing
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2012, 227 (03): : 341 - 342
  • [6] Crystal structure of (5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl furan-2-carboxylate, C10H7FN2O5
    Yan, Xiaowei
    Zhu, Dongjian
    Zhong, Xing
    Wang, Sujuan
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2018, 233 (05): : 843 - 844
  • [7] Synthesis, structural characterization and anticarcinogenic activity of a new Gly-Gly dipeptide derivative:: Methyl 2-(2-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetate
    Ping Yin
    Hu, Mao-Lin
    Hu, Li-Chuan
    JOURNAL OF MOLECULAR STRUCTURE, 2008, 882 (1-3) : 75 - 79
  • [8] Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate
    Ismail, El Fekki
    Ali, Ibrahim A. I.
    Fathalla, Walid
    Alsheikh, Amer A.
    El Tamney, El Said
    ARKIVOC, 2017, : 104 - 120
  • [9] Crystal structure of tert-butyl-3-(4-oxo-2-thioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate, C11H15N2O3S
    Yuan, Wei
    Liu, Jian-Ping
    Song, Xia
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2012, 227 (04): : 513 - 514
  • [10] Synthesis and Antimicrobial Activity of Novel Heterocycles Utilizing 3-(1,4-Dioxo-3,4-dihydrophthalazin-2(1H)-yl)-3-oxopropanenitrile as Precursors
    Khidre, Rizk E.
    Radini, Ibrahim Ali M.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (03) : 850 - 858