A METHOD FOR THE FACILE SYNTHESIS OF RING-A HYDROXYLATED FLAVONES

被引:38
作者
CUSHMAN, M
NAGARATHNAM, D
机构
[1] Department of Medicinal Chemistry, Pharmacognosy Purdue University, West Lafayette
关键词
D O I
10.1016/S0040-4039(00)97100-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general method for the facile synthesis of ring-A hydroxylated flavones is described. Treatment of the hydroxylated acetophenones 6a-d with enough lithium bis(trimethyl)silyl amide to deprotonate all of the phenols as well as to generate the lithium enolate of the ketone, followed by addition of the acid chlorides 7a-d, gave the 1,3-diketones 8a-g, which were cyclized to the desired products 9a-g in high yield. © 1990.
引用
收藏
页码:6497 / 6500
页数:4
相关论文
共 18 条
  • [1] C-13 NMR-STUDIES ON LICODIONE AND RELATED-COMPOUNDS IN EQUILIBRIUM MIXTURE OF KETO AND ENOL FORMS
    AYABE, SI
    FURUYA, T
    [J]. TETRAHEDRON LETTERS, 1980, 21 (31) : 2965 - 2968
  • [2] Molecular rearrangement of some o-acyloxyacetophenones and the mechanism of the production of 3-acylchromones
    Baker, W
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1933, : 1381 - 1389
  • [3] NATURAL-PRODUCTS AS A SOURCE OF POTENTIAL CANCER CHEMOTHERAPEUTIC AND CHEMOPREVENTIVE AGENTS
    CASSADY, JM
    BAIRD, WM
    CHANG, CJ
    [J]. JOURNAL OF NATURAL PRODUCTS, 1990, 53 (01): : 23 - 41
  • [4] GAYDOU EM, 1978, B SOC CHIM FR II-CH, P43
  • [5] INHIBITION OF PROTEIN-TYROSINE KINASE-ACTIVITY BY FLAVANOIDS AND RELATED-COMPOUNDS
    GEAHLEN, RL
    KOONCHANOK, NM
    MCLAUGHLIN, JL
    PRATT, DE
    [J]. JOURNAL OF NATURAL PRODUCTS, 1989, 52 (05): : 982 - 986
  • [6] FURTHER EXPERIMENTS ON THE MECHANISM OF THE BAKER-VENKATARAMAN TRANSFORMATION
    GOWAN, JE
    WHEELER, TS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1950, : 1925 - 1928
  • [7] HAGIWARA M, 1988, BIOCHEM PHARMACOL, V37, P2987
  • [8] HATANO T, 1988, CHEM PHARM BULL, V36, P2286
  • [9] HIRANO T, 1989, RES COMMUN CHEM PATH, V64, P69
  • [10] INHIBITION OF AVIAN-MYELOBLASTOSIS VIRUS REVERSE-TRANSCRIPTASE BY FLAVONES AND ISOFLAVONES
    INOUYE, Y
    YAMAGUCHI, K
    TAKE, Y
    NAKAMURA, S
    [J]. JOURNAL OF ANTIBIOTICS, 1989, 42 (10) : 1523 - 1525