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
  • [21] Selective synthesis of (3-ferrocenylprop-2-en-1-yl)-triphenylphosphonium iodide: crystal structure determination of two polymorphs
    Bouchene, Rafika
    Daran, Jean Claude
    Merazig, Hocine
    Manoury, Eric
    Bouacida, Sofiane
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2017, 73 : 376 - U51
  • [22] Synthesis of 2-(t-Butyl)dimethyl-silyloxy-2-cyclopropyl-1-ethyl-triphenylphosphonium iodide and Its Crystal Structure
    Wang, Wei
    Shen, Yong-Miao
    ASIAN JOURNAL OF CHEMISTRY, 2011, 23 (05) : 2227 - 2228
  • [23] (E)-1-Methyl-4-[2-(2-naphthyl)vinyl]-pyridinium iodide
    Fun, Hoong Kun
    Chanawanno, Kullapa
    Chantrapromma, Suchada
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O1406 - U2997
  • [24] Methyl (1R,2R)-and (1S,2S)-1-cyano-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropane-1-c arboxylate
    Universidad de Zaragoza-CZIC, Zaragoza, Spain
    Acta Crystallogr Sect C Cryst Struct Commun, pt 12 (3210-3213):
  • [25] HOMOLYTIC DISPLACEMENTS AT CARBON .8. SYNTHESIS OF 1-CYANO-2-(TRICHLOROETHYL)CYCLOPROPANES FROM ALLYLCOBALOXIMES VIA BUT-3-ENYLCOBALOXIMES AND 1-BROMO-1-CYANOBUT-3-ENES
    BURY, A
    CORKER, ST
    JOHNSON, MD
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (03): : 645 - 651
  • [26] 1-(2,5-dichlorophenyl)-2,2-bis(methylsulfanyl)vinyl esters as highly efficient chemoselective acylating reagents
    Degani, I
    Dughera, S
    Fochi, R
    Serra, E
    SYNTHESIS-STUTTGART, 1999, (07): : 1200 - 1208
  • [27] trans-Tetraaquabis{(E)-2-cyano-1-[(ethoxycarbonyl)methylsulfanyl]-2-(1-naphthylaminocarbonyl)ethene-1-thiolato}calcium(II) diethyl ether disolvate
    Elgemeie, Galal H.
    Fathy, Nahed M.
    Shaarawi, Sayed
    Jones, Peter G.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : M554 - U803
  • [28] Polynuclear Aromatic Amines as N-Nucleophiles in the ipso-Substitution of the Cyano Group in 1,2,4-Triazines
    Starnovskaya, E. S.
    Savchuk, M., I
    Shtaitz, Ya K.
    Kopchuk, D. S.
    Kovalev, I. S.
    Taniya, O. S.
    Pavlyuk, D. E.
    Khasanov, A. F.
    Zyryanov, G., V
    Chupakhin, O. N.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (02) : 335 - 338
  • [29] Synthesis of 4-amino-3-cyano-2methylsulfanyl-1 H-[1,5]benzodiazepine, benzo[1,3]azole, and pyrazolobenzo[1,3]azole derivatives via a new utility of bis(methylsulfanyl)methylene derivatives
    El-Rady, EA
    Khalil, MA
    El Latif, FMA
    HETEROATOM CHEMISTRY, 2004, 15 (05) : 407 - 412
  • [30] (E)-2-(4-tert-Butylphenyl)-2-cyano-1-(3-methyl-1-vinyl-1H-pyrazol-5-yl)vinyl 2,2-dimethylpropanoate
    Yang, Guiqiu
    Wang, Yang
    Yu, Haibo
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68 : O64 - +