Synthesis of 2-substituted furanonaphthoquinones using directed metalation and cross coupling reactions

被引:13
|
作者
Starling, SM
Raslan, DS
de Oliveira, AB
机构
[1] Univ Fed Minas Gerais, Fac Farm, BR-30180112 Belo Horizonte, MG, Brazil
[2] Univ Fed Minas Gerais, ICEx, Dept Quim, BR-30180112 Belo Horizonte, MG, Brazil
关键词
D O I
10.1080/00397919808003070
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthetic method for the preparation of C-2 substituted furanonaphthoquinones from ortholithium-benzamide and the 2-furan-carboxaldehyde derivative is described. Four 2-alkyl-furanonaphthoquinones and the 2-phenyl-substituted were prepared via phathalide. This route has been shown to be general application to the synthesis of furanonaphthoquinones.
引用
收藏
页码:1013 / 1030
页数:18
相关论文
共 50 条
  • [1] Synthesis of 2-substituted furanonaphthoquinones using directed metalation and cross coupling reactions
    Faculdade de Farmácia, Universidade Federal de Minas Gerais, Av. Olegário Maciel, 2360, Belo Horizonte, MG, CEP 30180-112, Brazil
    不详
    Synth. Commun., 6 (1013-1030):
  • [2] Regiospecific synthesis of 2-substituted furanonaphthoquinones
    Ohta, Y
    Doe, M
    Morimoto, Y
    Kinoshita, T
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (04) : 731 - 734
  • [3] Synthesis of 2-substituted dihydropyran 3-O-carbamates via combined metalation-Suzuki-Miyaura cross-coupling reactions
    Bower, JF
    Guillaneux, D
    Nguyen, T
    Wong, PL
    Snieckus, V
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (05): : 1514 - 1518
  • [4] Linked directed ortho metalation-cross coupling reactions
    Snieckus, Victor
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [5] SYNTHESIS AND COUPLING REACTIONS OF 2-SUBSTITUTED 3-OXEPANONES
    DAVIES, MJ
    MOODY, CJ
    TAYLOR, RJ
    SYNLETT, 1990, (02) : 93 - 94
  • [6] THE N-TERT-BUTYLCARBAMOYL DIRECTED METALATION GROUP FOR THE REGIOSPECIFIC SYNTHESIS OF 2-SUBSTITUTED PYRROLES AND INDOLES
    GHARPURE, M
    STOLLER, A
    BELLAMY, F
    FIRNAU, G
    SNIECKUS, V
    SYNTHESIS-STUTTGART, 1991, (12): : 1079 - 1082
  • [7] A NEW GENERAL-SYNTHESIS OF PHENANTHRENES USING DIRECTED METALATION CROSS COUPLING APPROACH
    FU, JM
    SHARP, MJ
    SNIECKUS, V
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 195 : 66 - ORGN
  • [8] DIRECTED METALATION REACTIONS .5. METALATION AND REARRANGEMENT IN SUBSTITUTED 2-THIOPHENESULFONAMIDES
    SLOCUM, DW
    GIERER, PL
    JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (24): : 4189 - 4192
  • [9] The Directed ortho Metalation -: Cross-coupling symbiosis in heteroaromatic synthesis
    Green, L
    Chauder, B
    Snieckus, V
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (06) : 1453 - 1468
  • [10] DIRECTED METALATION REACTIONS .4. METALATION-2 OF N-SUBSTITUTED FERROCENECARBOXAMIDES
    SLOCUM, DW
    STONEMAR.FE
    JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (09): : 1677 - 1681