PHOTOCHEMICAL TRIFLUOROMETHYLATION OF 1-METHYLIMIDAZOLES AND 1-METHYLPYRROLES CONTAINING METHYLTHIO GROUPS

被引:14
作者
NISHIDA, M [1 ]
KIMOTO, H [1 ]
FUJII, S [1 ]
HAYAKAWA, Y [1 ]
COHEN, LA [1 ]
机构
[1] NIDDKD, BIOORGAN CHEM LAB, BETHESDA, MD 20892 USA
关键词
D O I
10.1246/bcsj.64.2255
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The title reaction was achieved by UV (254 nm) irradiation with CF3I. The methylthio group was introduced to increase electron density and to limit available reactive sites in the rings. Following trifluoromethylation, the methylthio groups were readily removed by hydrogenolysis (Raney Ni) to give the desired trifluoromethyl heterocycles.
引用
收藏
页码:2255 / 2259
页数:5
相关论文
共 28 条
  • [1] ASSEF G, 1976, TETRAHEDRON LETT, P3313
  • [2] 4-TRIFLUOROMETHYLIMIDAZOLES AND 5-(4-PYRIDYL)-1,2,4-TRIAZOLES, NEW CLASSES OF XANTHINE-OXIDASE INHIBITORS
    BALDWIN, JJ
    KASINGER, PA
    NOVELLO, FC
    SPRAGUE, JM
    DUGGAN, DE
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (09) : 895 - 900
  • [3] CARPENTER AJ, 1983, MINIPRINT, P1913
  • [4] CARPENTER AJ, 1983, J CHEM RES S, P196
  • [5] NEW SYNTHESIS OF 2-NITROIMIDAZOLES
    DAVIS, DP
    KIRK, KL
    COHEN, LA
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (02) : 253 - 256
  • [6] C-13 NMR-STUDY OF SUBSTITUENT EFFECTS IN 1,3-DIAZOLE AND 1,3-DIAZINE SERIES
    FAURE, R
    VINCENT, EJ
    ASSEF, G
    KISTER, J
    METZGER, J
    [J]. ORGANIC MAGNETIC RESONANCE, 1977, 9 (12): : 688 - 694
  • [7] SYNTHESIS AND ALKALINE-HYDROLYSIS OF (PENTAFLUOROETHYL)-IMIDAZOLES
    FUJII, S
    MAKI, Y
    KIMOTO, H
    COHEN, LA
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 1987, 35 (03) : 437 - 454
  • [8] SULFUR DERIVATIVES OF 1-METHYLPYRROLE
    GRONOWITZ, S
    KADA, R
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (04) : 1041 - 1043
  • [9] ACTION OF RANEY NICKEL ON ORGANIC SULFUR COMPOUNDS
    HAUPTMANN, H
    WALTER, WF
    [J]. CHEMICAL REVIEWS, 1962, 62 (05) : 347 - &
  • [10] THE DEGRADATION OF SILVER TRIFLUOROACETATE TO TRIFLUOROIODOMETHANE
    HENNE, AL
    FINNEGAN, WG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (08) : 3806 - 3807