Cyclocondensation of [1-Cyano-2-(methylsulfanyl)vinyl]triphenylphosphonium Iodide with Amidine Nucleophiles

被引:0
|
作者
O. B. Smolii
L. V. Muzychka
A. N. Chernega
B. S. Drach
机构
[1] National Academy of Sciences of Ukraine,Institute of Bioorganic Chemistry and Petrochemistry
来源
关键词
Iodide; Vinyl; Pyrimidine; Amidine; Benzamidine;
D O I
暂无
中图分类号
学科分类号
摘要
The substituted vinylphosphonium salt (E)-MeSCH=C(CN)P+Ph3I− readily cyclizes under the action of benzamidine and 3-amino-s-triazole, but it does not enter cyclocondensation with 2-aminopyridine. The structure of the cyclization product with 3-amino-s-triazole was confirmed by its transformation to 7-imino-6-(triphenylphosphoranylidene)-6,7-dihydro-s-triazolo[1,5]pyrimidine which was identified by X-ray diffraction. This stabilized ylide and its analogs proved useful starting materials for regioselective syntheses of 2-R-4-alkyl-4,7-dihydro-s-triazolo[1,5-a]pyrimidin-7-ones.
引用
收藏
页码:527 / 532
页数:5
相关论文
共 50 条
  • [31] Polynuclear Aromatic Amines as N-Nucleophiles in the ipso-Substitution of the Cyano Group in 1,2,4-Triazines
    E. S. Starnovskaya
    M. I. Savchuk
    Ya. K. Shtaitz
    D. S. Kopchuk
    I. S. Kovalev
    D. E. Pavlyuk
    A. F. Khasanov
    G. V. Zyryanov
    O. N. Chupakhin
    Russian Journal of Organic Chemistry, 2020, 56 : 335 - 338
  • [32] THE REACTION OF 2-CHLORO-10-N-METHYLPHENOTHIAZINE WITH AROMATIC NITRILES AND LITHIUM DIALKYLAMIDES IN THF - SYNTHESIS AND STRUCTURE OF 1-CYANO-2-(3',4',5'-TRIMETHOXYBENZYL)-10-N-METHYLPHENOTHIAZINE
    BIEHL, ER
    KHANAPURE, SP
    SIRIWARDANE, U
    TSCHANTZ, M
    HETEROCYCLES, 1989, 29 (03) : 485 - 494
  • [33] ELECTROCHEMICAL OXIDATION OF 2,4,6-TRI TERT BUTYL-ANILINE IN PRESENCE OF PYRIDINIC NUCLEOPHILES .1. PREPARATION OF [-1,2-A]-BENZIMIDAZOLES AND OF AN AMIDINE
    CAUQUIS, G
    CROS, JL
    GENIES, M
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1971, (10): : 3765 - &
  • [34] HISTAMINE-H2 RECEPTOR ANTAGONISTS .1. SYNTHESIS OF N-CYANO AND N-CARBAMOYL AMIDINE DERIVATIVES AND THEIR BIOLOGICAL-ACTIVITIES
    YANAGISAWA, I
    HIRATA, Y
    ISHII, Y
    JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (07) : 849 - 857
  • [35] STRUCTURES OF 1-CYANO-2,2-BIS(METHYLTHIO)VINYL N,N-DIMETHYLDITHIOCARBAMATE (2) AND 1,2,2-TRIS(METHYLTHIO)VINYL N,N-DIMETHYLDITHIOCARBAMATE (3)
    HEINEMANN, F
    DOLLING, W
    HARTUNG, H
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1992, 48 : 2266 - 2268
  • [36] 2-alkyl- and 2-cyano-substituted 1-acyl-3,4-epoxy-1,2,3,4-tetrahydroquinoline - Reactions with O-nucleophiles
    Hiessbock, R
    Kratzel, M
    HETEROCYCLES, 1996, 43 (04) : 873 - 882
  • [37] Using a Fluorescent 1-Methyl-4-(2-Pyren-1-Yl-Vinyl)-Pyridinium Iodide to Characterize Solvent Polarities
    Cao, X.
    Yi, H.
    Li, L.
    Zhang, S.
    Pan, H.
    Chen, J.
    Xu, J.
    JOURNAL OF APPLIED SPECTROSCOPY, 2018, 84 (06) : 939 - 947
  • [38] Using a Fluorescent 1-Methyl-4-(2-Pyren-1-Yl-Vinyl)-Pyridinium Iodide to Characterize Solvent Polarities
    X. Cao
    H. Yi
    L. Li
    S. Zhang
    H. Pan
    J. Chen
    J. Xu
    Journal of Applied Spectroscopy, 2018, 84 : 939 - 947
  • [39] 2-(2,2-Bis-benzylamino-1-cyano-vinyl)-benzonitrile: A Selective Turn-off Fluorescent Cu2+ Sensor
    Singh, Surjeet
    Reddy, T. Sheshashena
    Panwar, Rahul
    Misra, Rajneesh
    Pratap, Ramendra
    CHEMISTRYSELECT, 2016, 1 (11): : 2576 - 2580
  • [40] SODIUM BOROHYDRIDE REDUCTION OF 1-METHYL-3-CYANO-PYRIDINE IODIDE . EXPERIMENTAL BASES FOR INTERPRETATION OF ORIGIN OF 1,2,5,6-TETRAHYDROPYRIDINE
    LIBERATORE, F
    CARELLI, V
    CARDELLI.M
    CHIMICA & L INDUSTRIA, 1969, 51 (01): : 55 - +