Synthesis of New Perfluoroalkylated 1,3,4-Oxadiazoles and 1,2,4-Triazoles Starting from 2-(Perfluoroalkyl)ethane Thiols

被引:3
作者
Akremi, Ali [1 ]
Beji, Mohamed [1 ]
Baklouti, Ahmed [1 ]
机构
[1] Fac Sci Tunis, Dept Chem, Lab Struct Organ Chem, Tunis 2092, Tunisia
关键词
Aryloxysulfonylisocyanates; carbon disulfide; 1; 3; 4-oxadiazole; 2-(perfluoroalkyl)ethane thiols; 2; 4-triazole; DERIVATIVES; DESIGN;
D O I
10.1080/00397911.2010.494816
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[image omitted] 5-{[2-(Perfluoroalkyl)ethylthio]methyl}-1,3,4-oxadiazole-2-thiones 4a, b and 4-amino-5-{[2-(perfluoroalkyl)ethylthio]methyl}-4H-1,2,4-triazole-3-thiones 5a, b have been prepared from 2-(perfluoroalkyl)ethane thiols 1a, b through a multistep reaction sequence. Compounds 4a, b were further reacted with aryloxysulfonylisocyanates to give the corresponding 5-{[2-(perfluoroalkyl)ethylthio]methyl}-N-(aryloxysulfonyl)-2-thioxo-1,3,4-oxadiazole-3(2H)-carboxamide 6a-d. The new products were obtained in good to moderate yields, and their structures were established on the basis of their infrared, NMR, and mass spectral data.
引用
收藏
页码:1990 / 1998
页数:9
相关论文
共 50 条
  • [21] Synthesis of Novel Derivatives of 1,2,4-Triazoles
    Galstyan, Armen S.
    Ghochikyan, Tariel, V
    Frangyan, Vardges R.
    Tamazyan, Rafael A.
    Ayvazyan, Armen G.
    CHEMISTRYSELECT, 2018, 3 (35): : 9981 - 9985
  • [22] Synthesis of New Substituted 1,2,4-Triazoles and 1,3,4-Thiadiazoles and Their Effects on DNA Methylation Level
    Hovsepyan, T. R.
    Hakobyan, M. R.
    Muradyan, R. E.
    Nersesyan, L. E.
    Agaronyan, A. S.
    Danielyan, I. S.
    Minasyan, N. S.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2019, 89 (04) : 673 - 679
  • [23] Propylphosphonic anhydride (T3P®): an efficient reagent for the one-pot synthesis of 1,2,4-oxadiazoles, 1,3,4-oxadiazoles, and 1,3,4-thiadiazoles
    Augustine, John Kallikat
    Vairaperumal, Veeramani
    Narasimhan, Sharmila
    Alagarsamy, Padma
    Radhakrishnan, Anbarasi
    TETRAHEDRON, 2009, 65 (48) : 9989 - 9996
  • [24] Formal [4+1] cyclization of (thio/imido)hydrazides and ethyl 3,3,3-trifluoropropanoate: unified synthesis of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles
    Zhao, Lan
    Xu, Jun
    Ma, Jun
    Yin, Guangwei
    Li, Fangyi
    Suo, Tongchuan
    Wang, Chunhua
    NEW JOURNAL OF CHEMISTRY, 2022, 46 (43) : 20755 - 20759
  • [25] Isoxazol-3-yl(Isothiazol-3-yl)-1,2,4-Triazoles, -Tetrazoles, and-1,3,4-Oxadiazoles: Synthesis, Palladium Complexes, and Catalytic Applications
    Bumagin, N. A.
    Petkevich, S. K.
    Kletskov, A. V.
    Livantsov, M. V.
    Golantsov, N. E.
    Potkin, V. I.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 49 (10) : 1515 - 1529
  • [26] Synthesis of novel sulfonamide-1,2,4-triazoles, 1,3,4-thiadiazoles and 1,3,4-oxadiazoles, as potential antibacterial and antifungal agents. Biological evaluation and conformational analysis studies
    Zoumpoulakis, P.
    Camoutsis, Ch.
    Pairas, G.
    Sokovic, M.
    Glamoclija, J.
    Potamitis, C.
    Pitsas, A.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (04) : 1569 - 1583
  • [27] Synthesis and Antimicrobial Assessment of Some New 2-(Thiazol-5-yl)-1,3,4-oxadiazoles
    Araniciu, Catalin
    Oniga, Smaranda Dafina
    Stoica, Cristina Ioana
    Chifiriuc, Mariana Carmen
    Popa, Marcela
    Vlase, Laurian
    Palage, Mariana
    Oniga, Ovidiu
    REVISTA DE CHIMIE, 2019, 70 (06): : 1996 - 1999
  • [28] Rapid, microwave accelerated synthesis of [1,2,4]triazolo[3,4-b] [1,3,4]oxadiazoles from 4-acylamino-1,2,4-triazoles
    Breunig, Stephanie L.
    Olson, Margaret E.
    Harki, Daniel A.
    TETRAHEDRON LETTERS, 2016, 57 (36) : 4056 - 4060
  • [29] Bronsted acid-catalyzed simple and efficient synthesis of 1,2,4-triazoles and 1,2,4-oxadiazoles using 2,2,2-trichloroethyl imidates in PEG
    Nakka, Mangarao
    Gajula, Mahaboob Basha
    Tadikonda, Ramu
    Rayavarapu, Srinuvasarao
    Sarakula, Prasanthi
    Vidavalur, Siddaiah
    TETRAHEDRON LETTERS, 2014, 55 (01) : 177 - 179
  • [30] 2-(4-Biphenylyl)-1,3,4-oxadiazoles: synthesis and mesogenic studies
    Fouad, Farid
    Davis, David R.
    Twieg, Robert
    LIQUID CRYSTALS, 2018, 45 (10) : 1508 - 1517