FUNCTIONALIZED O-BIS(CHLOROMETHYL)PYRIDINES AS PRECURSORS FOR PYRIDINE O-QUINODIMETHANE ANALOGS AND THEIR [4+2] CYCLOADDUCTS

被引:22
作者
CARLY, PR [1 ]
COMPERNOLLE, F [1 ]
HOORNAERT, GJ [1 ]
机构
[1] KATHOLIEKE UNIV LEUVEN,DEPT CHEM,ORGAN SYNTH LAB,B-3001 HEVERLEE,BELGIUM
关键词
D O I
10.1016/0040-4039(95)00169-D
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
From oxazinoes 4, precursors for pyridine o-quinodimethane analogues are made accessible via cycloaddition with 1,4-dichloro-2-butyne and propargyl chloride. Subsequent 1,4-elimination of the polyfunctional o-bis(chloromethyl)-pyridines affords both 2,3- and 3,4-dimethylene compounds, which are trapped in situ with various dienophiles.
引用
收藏
页码:2113 / 2116
页数:4
相关论文
共 9 条
  • [1] CONDENSED CYCLOBUTANE AROMATIC SYSTEMS .2. DIHALO DERIVATIVES OF BENZOCYCLOBUTENE AND BENZOCYCLOBUTADIENE DIMER
    CAVA, MP
    NAPIER, DR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (07) : 1701 - 1705
  • [2] CHOU TS, 1993, REV HETEROATOM CHEM, V8, P65
  • [3] SYNTHESES OF POLYCYCLIC RING-SYSTEMS BASED ON THE NEW GENERATION OF ORTHO-QUINODIMETHANES
    ITO, Y
    NAKATSUKA, M
    SAEGUSA, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (26) : 7609 - 7622
  • [4] KAMETANI T, 1974, HETEROCYCLES, V2, P171
  • [5] RECENT ADVANCES IN ORTHO-QUINODIMETHANE CHEMISTRY
    MARTIN, N
    SEOANE, C
    HANACK, M
    [J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1991, 23 (02) : 237 - &
  • [6] MEERPOEL L, 1990, SYNTHESIS-STUTTGART, P905
  • [7] FUNCTIONALIZATION IN POSITION-3 OF 3,5-DICHLORO-2H-1,4-OXAZIN-2-ONES
    VANAKEN, KJ
    MEERPOEL, L
    HOORNAERT, GJ
    [J]. TETRAHEDRON LETTERS, 1992, 33 (19) : 2713 - 2716
  • [8] THE SYNTHESIS OF 3-FUNCTIONALIZED 5-CHLORO-6-METHYL-2H-1,4-OXAZIN-2-ONES AND OF PYRIDINES FROM CYCLOADDITION-ELIMINATION REACTIONS WITH SUBSTITUTED ACETYLENIC-COMPOUNDS
    VANAKEN, KJ
    LUX, GM
    DEROOVER, GG
    MEERPOEL, L
    HOORNAERT, GJ
    [J]. TETRAHEDRON, 1994, 50 (17) : 5211 - 5224
  • [9] INDOLE-2,3-QUINODIMETHANES - GENERATION, REACTIVITY AND REGIOSELECTIVE CONTROL OF INTERMOLECULAR DIELS-ALDER REACTIONS
    VICE, SF
    DECARVALHO, HN
    TAYLOR, NG
    DMITRIENKO, GI
    [J]. TETRAHEDRON LETTERS, 1989, 30 (52) : 7289 - 7292