Formation and reduction reactions of 3-indol-3-yl-isoxazolidines

被引:19
作者
CoutouliArgyropoulou, E
MalamidouXenikaki, E
Stampelos, XN
Alexopoulou, IN
机构
[1] Department of Chemistry, Aristotelian Univ. of Thessaloniki
关键词
D O I
10.1016/S0040-4020(96)01013-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,3-Dipolar cycloaddition reactions of C-(1-methylindol-3-yl)-N-methylnitrone (1) with carbonyl substituted dipolarophiles lead to the formation of indolyl-isoxazolidines 3-6. Further reduction of the cycloadducts bearing a 5-methoxycarbonyl substituent give the pyrrolidinones 8,10. The stereoselectivity of the reactions and the structure elucidation of the products are discussed. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:707 / 718
页数:12
相关论文
共 24 条
  • [1] 1,3-DIPOLAR CYCLOADDITION REACTIONS OF A HETEROCYCLIC NITRONE
    ALI, SA
    ALMUALLEM, HA
    [J]. TETRAHEDRON, 1992, 48 (25) : 5273 - 5282
  • [2] ALI SA, 1978, TETRAHEDRON LETT, P4167
  • [3] NEW ASPECTS IN THE HYDROGENOLYTIC OPENING OF 2-ISOXAZOLINES
    AURICCHIO, S
    RICCA, A
    [J]. TETRAHEDRON, 1987, 43 (17) : 3983 - 3986
  • [4] AURICH HG, 1994, TETRAHEDRON, V50, P7417
  • [5] SYNTHESIS AND CHARACTERIZATION OF NEW INDOLE TRIMERS AND TETRAMERS
    BOCCHI, V
    PALLA, G
    [J]. TETRAHEDRON, 1986, 42 (18) : 5019 - 5024
  • [6] FORMATION OF OXADIAZOLO[4,5-A]INDOLINES VIA ADDITION-REACTIONS OF CYCLOALKANO[B]INDOLES WITH NITRILE OXIDES - CRYSTAL-STRUCTURE OF AN ADDUCT
    COUTOULIARGYROPOULOU, E
    MALAMIDOUXENIKAKI, E
    MENTZAFOS, D
    TERZIS, A
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (05) : 1185 - 1189
  • [7] CURRAN DP, 1988, ADV CYCLOADDITION, V1, P129
  • [8] STRUCTURE OF HYDROXYCOTININE, A NICOTINE METABOLITE
    DAGNE, E
    CASTAGNOLI, N
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (04) : 356 - +
  • [9] DOYLE KJ, 1994, SYNTHESIS-STUTTGART, P1021
  • [10] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .2. OXIME CYCLO-ADDITIONS - FORMATION OF 2-1 ADDUCTS
    GRIGG, R
    JORDAN, M
    TANGTHONGKUM, A
    EINSTEIN, FWB
    JONES, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (01): : 47 - 57