Experimental and theoretical study on 6-substituted pyridoxine derivatives. Synthesis of cyclic 2,4,5,6-tetrakis-(hydroxymethyl)pyridin-3-ol acetonides

被引：0
|
作者：
N. V. Shtyrlin
A. B. Dobrynin
T. I. Madzhidov
M. V. Pugachev
L. P. Sysoeva
R. Z. Musin
I. A. Litvinov
E. N. Klimovitskii
Yu. G. Shtyrlin
机构：
[1] Kazan (Privolzhsk) Federal University,Butlerov Institute of Chemistry
[2] Russian Academy of Sciences,Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center
来源：
Russian Journal of Organic Chemistry | 2011年 / 47卷
关键词：
Acetic Anhydride; Hydroxymethyl Group; Sodium Ethoxide; Column Chroma; Hydrogen Bond Parameter;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Synthetic approaches to three cyclic 2,4,5,6-tetrakis(hydroxymethyl)pyridin-3-ol acetonides were developed. Among seven possible mono- and diketals, six-membered cyclic ketal incorporating the hydroxymethyl group in the 4-position turned out to be the most thermodynamically favorable. The experimental data were consistent with the results of quantum-chemical calculations of the Gibbs energies of formation of different acetonides. The structure of the isolated compounds was studied by X-ray diffraction.
引用
收藏
页码：100 / 108
页数：8
相关论文
共 24 条
  • [1] Experimental and Theoretical Study on 6-Substituted Pyridoxine Derivatives. Synthesis of Cyclic 2,4,5,6-Tetrakis-(hydroxymethyl)pyridin-3-ol Acetonides
    Shtyrlin, N. V.
    Dobrynin, A. B.
    Madzhidov, T. I.
    Pugachev, M. V.
    Sysoeva, L. P.
    Musin, R. Z.
    Litvinov, I. A.
    Klimovitskii, E. N.
    Shtyrlin, Yu. G.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 47 (01) : 100 - 108
  • [2] Theoretical and experimental study on cyclic 6-methyl-2,3,4-tris(hydroxymethyl)pyridin-5-ol acetonides
    N. V. Shtyrlin
    O. A. Lodochnikova
    M. V. Pugachev
    T. I. Madzhidov
    L. P. Sysoeva
    I. A. Litvinov
    E. N. Klimovitskii
    Yu. G. Shtyrlin
    Russian Journal of Organic Chemistry, 2010, 46 : 561 - 567
  • [3] Theoretical and experimental study on cyclic 6-methyl-2,3,4-tris(hydroxymethyl)pyridin-5-ol acetonides
    Shtyrlin, N. V.
    Lodochnikova, O. A.
    Pugachev, M. V.
    Madzhidov, T. I.
    Sysoeva, L. P.
    Litvinov, I. A.
    Klimovitskii, E. N.
    Shtyrlin, Yu. G.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (04) : 561 - 567
  • [4] SYNTHETIC STUDIES ON PYRIDOXINE DERIVATIVES .1. SYNTHESIS OF 5-SUBSTITUTED-3-(2-METHYL-3-HYDROXY-5-HYDROXYMETHYL-4-PYRIDYL)METHYL-4-METHYLTHIAZOLINE-2-THIONES
    ITO, I
    KUROYANAGI, Y
    SUZUKI, K
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1975, 95 (08): : 944 - 948
  • [5] Sonochemical Synthesis of 6-Substituted Indolo[3′,2′:4,5]pyrrolo[2,3-b]quinoxaline Derivatives as Potential Cytotoxic Agents
    Rao, Mandava V. B.
    SriLaxmi, Dandamudi
    Vardhini, Suryadevara V.
    Guttikonda, Venkata R.
    Kapavarapu, Ravikumar
    Pal, Manojit
    CHEMISTRYSELECT, 2020, 5 (45): : 14239 - 14246
  • [6] SYNTHESIS OF NEW 2, 5, 6-SUBSTITUTED IMIDAZO[2,1-B][1,3,4]THIADIAZOLE DERIVATIVES AS POTENTIAL ANTICANCER AGENTS
    Sethi, Navdeep Singh
    Noolvi, Malleshappa N.
    Kharb, Vandana
    Nathubhai, Vinay K.
    More, Uttam A.
    Avvaru, Stephen Paul
    Khairnar, Bhikan J.
    Desai, Shivali
    Thippeswamy, B. S.
    Al Otaibi, Faisal
    INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES AND RESEARCH, 2020, 11 (11): : 5518 - 5529
  • [7] Synthesis and anticancer activity of new 1-[(5 or 6-substituted 2-alkoxyquinoxalin-3-yl)aminocarbonyl]-4-(hetero)arylpiperazine derivatives
    Lee, Young Bok
    Gong, Young-Dae
    Yoon, Heejeong
    Ahn, Chang-Ho
    Jeon, Moon-Kook
    Kong, Jae-Yang
    BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (22) : 7966 - 7974
  • [8] Synthesis of 6-substituted pyrido[3,4-d]-pyrimidin-4(3H)-ones via directed lithiation of 2-substituted 5-aminopyridine derivatives
    Rewcastle, G. W.
    Denny, W. A.
    Winters, R. T.
    Colbry, N. L.
    Jornal of the Chemical Society. Perkin Transactions 1, (18):
  • [9] Synthesis of 6-substituted pyrido[3,4-d]pyrimidin-4(3H)-ones via directed lithiation of 2-substituted 5-aminopyridine derivatives
    Rewcastle, GW
    Denny, WA
    Winters, RT
    Colbry, NL
    Showalter, HDH
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (18): : 2221 - 2226
  • [10] Synthesis and antisecretory activity of 6-substituted 5-cyanomethylimidazo[2,1-b]-thiazoles and 2,6-dimethyl-5-hydroxymethyl imidazo[2,1-b][1,3,4]thiadiazole
    Andreani, A
    Leoni, A
    Locatelli, A
    Morigi, R
    Rambaldi, M
    Simon, WA
    Senn-Bilfinger, J
    ARZNEIMITTEL-FORSCHUNG-DRUG RESEARCH, 2000, 50 (06): : 550 - 553
123