N-vinyl-nitroimidazole cycloadditions:: Potential routes to nucleoside analogues

被引:10
作者
Clayton, R [1 ]
Ramsden, CA [1 ]
机构
[1] Univ Keele, Sch Chem & Phys, Lennard Jones Labs, Keele ST5 5BG, Staffs, England
来源
SYNTHESIS-STUTTGART | 2005年 / 16期
关键词
nitroimidazole; vinylimidazole; 1,3-dipolar cycloadditions; isoxazoline; nucleoside analogues;
D O I
10.1055/s-2005-872083
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cycloaddition reactions of 4-nitro- and 5-nitro-1-vinylimidazoles have been investigated. The cycloadducts obtained are potential intermediates for synthesis of purine nucleoside analogues via reduction to the corresponding aminomidazoles. A byproduct obtained using benzonitrile oxide as 1,3-dipolarophile has been identified as a novel tricyclic isomer 12 of the cycloadduct it.
引用
收藏
页码:2695 / 2700
页数:6
相关论文
共 22 条
  • [11] Humphries MJ, 1999, SYNTHESIS-STUTTGART, P985
  • [12] HUMPHRIES MJ, 1995, SYNLETT, P203
  • [13] 5-amino-1,2-dimethylimidazole
    Jones, RH
    Lothian, AP
    Ramsden, CA
    [J]. ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 1996, 52 : 982 - 984
  • [14] A PARTICULARLY CONVENIENT PREPARATION OF BENZOHYDROXIMINOYL CHLORIDES (NITRILE OXIDE PRECURSORS)
    LIU, KC
    SHELTON, BR
    HOWE, RK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (19) : 3916 - 3918
  • [15] 4-UNSUBSTITUTED, 5-AMINO AND 5-UNSUBSTITUTED, 4-AMINOIMIDAZOLES
    LYTHGOE, DJ
    RAMSDEN, CA
    [J]. ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 61, 1994, 61 : 1 - 58
  • [16] MCFADZEAN JA, 1986, FLAGYL STORY PHARM D
  • [17] 4-NITROIMIDAZOLES AND 5-NITROIMIDAZOLES - C-13 NMR ASSIGNMENT OF STRUCTURE
    MCKILLOP, A
    WRIGHT, DE
    PODMORE, ML
    CHAMBERS, RK
    [J]. TETRAHEDRON, 1983, 39 (22) : 3797 - 3800
  • [18] THE REACTIONS OF PRIMARY NITROPARAFFINS WITH ISOCYANATES
    MUKAIYAMA, T
    HOSHINO, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (20) : 5339 - 5342
  • [19] DIPOLAR CYCLOADDITION REACTIONS OF N-TETRAHYDROPYRANYLNITRONE
    MZENGEZA, S
    WHITNEY, RA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (09) : 606 - 607
  • [20] RAMSDEN CA, 1995, CHEM HETEROCYCL COMP, P1323