A REINVESTIGATION OF THE SYNTHESIS OF TRANS-(+/-)-1,2,3,4-4A,10A-HEXAHYDRO[1,4]BENZODIOXINO[2,3-C]PYRIDINE

被引：6
作者：
PROCOPIOU, PA
CHERRY, PC
DEAL, MJ
LAMONT, RB
机构：
[1] Glaxo Research and Development Limited, Greenford, Middlesex
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 13期
关键词：
D O I：
10.1039/p19940001773
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A reinvestigation of the reaction of threo-(+/-)-2,3-dibromopentane-1,5-diol 5 with the disodium salt of catechol has shown that the product is (+/-)-1-(2,3-dihydro[1,4]benzodioxin-2-yl)propane-1,3-diol 20 and not trans-(+/-)-3-(2-hydroxyethyl)-2-(hydroxymethyl) -2,3-dihydro[1,4]benzodioxin 12, as assumed previously. Consequently trans-(+/-)-1,2,3,4,4a,10a-hexahydro[1,4]benzodioxino[2.3-c] pyridine 3 could not have been isolated earlier, and we now report its unambiguous synthesis via the epoxide 8 as well as the crystal structure of the diol 20.
引用
收藏
页码：1773 / 1777
页数：5
相关论文
共 9 条
  • [1] MODIFIED PRINS REACTION APPLICABLE TO CONJUGATED DIENES
    BAJOREK, JJS
    BATTAGLI.R
    PRATT, G
    SUTHERLA.JK
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (11): : 1243 - 1245
  • [2] TRIPHENYLPHOSPHINE-TETRACHLOROMETHANE PROMOTED CHLORINATION AND CYCLODEHYDRATION OF SIMPLE DIOLS
    BARRY, CN
    EVANS, SA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (16) : 3361 - 3364
  • [3] SYNTHESIS OF CIS- AND TRANS-1,2,3,4,4A,10A-HEXAHYDRO-1,4-BENZODIOXINO 2,3-C!PYRIDINES
    BERTHOLD, R
    NIKLAUS, P
    STOLL, AP
    TROXLER, F
    [J]. HELVETICA CHIMICA ACTA, 1970, 53 (05) : 1128 - &
  • [4] SYNTHESIS OF 1,2,3,4,4A,10A-HEXAHYDROPYRIDO[3,4-B][1,4]BENZODIOXINS
    COULSON, CJ
    WOOLDRID.KR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (19): : 2830 - &
  • [5] REINVESTIGATION OF SYNTHESIS OF CIS-1,2,3,4,4A,10A-HEXAHYDRO[1,4]BENZODIOXINO[2,3-C]PYRIDINE AND A SYNTHESIS OF MESO-2,3,4,5,5A,11A-HEXAHYDRO-1H-[1,4]BENZODIOXINO[2,3-D]AZEPINE
    FINCH, N
    BLANCHARD, L
    WERNER, LH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (24) : 3933 - 3937
  • [6] THE PHARMACOLOGY OF FLUPAROXAN - A SELECTIVE ALPHA-2-ADRENOCEPTOR ANTAGONIST
    HALLIDAY, CA
    JONES, BJ
    SKINGLE, M
    WALSH, DM
    WISE, H
    TYERS, MB
    [J]. BRITISH JOURNAL OF PHARMACOLOGY, 1991, 102 (04) : 887 - 895
  • [7] TETRAHYDROPYRAN-3-4-DIOL AND TETRAHYDRO-2-2-5-5-TETRAMETHYLFURAN-3-4-DIOL
    HEUBERGER, O
    OWEN, LN
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1952, (MAR): : 910 - 914
  • [8] A NOVEL CYCLODEHYDRATION REACTION OF HYDROXY-PHENOLS USING IMIDATE ESTERS AS LEAVING GROUPS
    PROCOPIOU, PA
    BRODIE, AC
    DEAL, MJ
    HAYMAN, DF
    [J]. TETRAHEDRON LETTERS, 1993, 34 (46) : 7483 - 7486
  • [9] SHELDRICK GM, 1990, SHELXTL PLUS RELEASE
1