APPLICATION OF ORGANOLITHIUM AND RELATED REAGENTS IN SYNTHESIS .13. SYNTHETIC STRATEGIES BASED ON AROMATIC METALATION - A CONCISE REGIOSPECIFIC CONVERSION OF BENZOIC-ACIDS INTO 4-HYDROXY-1-ARYLNAPHTHALENES

被引:22
作者
EPSZTAJN, J
JOZWIAK, A
SZCZESNIAK, AK
机构
关键词
D O I
10.1016/S0040-4020(01)80334-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of the 3-unsubstituted phthalides (S) and their conversion into 1-hydroxy-1-arylphthalans (8), very useful precursors of isobenzofurans (10) and subsequent cycloaddition of them to dimethyl acetylenedicarboxylate as a way of regiospecific transformation of benzoic acids into dimethyl 4-hydroxy-1-(2-methoxyphenyl)naphthalene-2,3-dicarboxylates (12) (biaryls highly substituted around the axis), is described.
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页码:929 / 938
页数:10
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共 27 条
  • [1] DIRECTED LITHIATION OF AROMATIC TERTIARY AMIDES - AN EVOLVING SYNTHETIC METHODOLOGY FOR POLYSUBSTITUTED AROMATICS
    BEAK, P
    SNIECKUS, V
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (10) : 306 - 312
  • [2] THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES
    BRINGMANN, G
    WALTER, R
    WEIRICH, R
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09): : 977 - 991
  • [3] BUCHLER CA, 1944, J AM CHEM SOC, V66, P417
  • [4] CHAKRAVARTI SN, 1934, J INDIAN CHEM SOC, V11, P873
  • [5] DUBININ BM, 1935, DOKL AKAD NAUK SSSR, V3, P236
  • [6] APPLICATION OF ORGANOLITHIUM AND RELATED REAGENTS IN SYNTHESIS .12. SYNTHESIS OF PHENYLPYRIDOPYRIDAZINONES AND PYRIDYLPYRIDOPYRIDAZINONES AND THEIR DERIVATIVES
    EPSZTAJN, J
    BRZEZINSKI, JZ
    CZECH, K
    [J]. MONATSHEFTE FUR CHEMIE, 1993, 124 (05): : 549 - 558
  • [7] APPLICATION OF ORGANOLITHIUM AND RELATED REAGENTS IN SYNTHESIS .10. METALATION-ELECTROPHILIC SUBSTITUTION SEQUENCE OF SECONDARY CHLOROBENZAMIDES
    EPSZTAJN, J
    BIENIEK, A
    KOWALSKA, JA
    SCIANOWSKI, J
    [J]. MONATSHEFTE FUR CHEMIE, 1992, 123 (12): : 1125 - 1134
  • [8] PERI-HYDROXYCARBONYL COMPOUNDS .2. THE EFFECT OF RING SIZE ON HYDROGEN BONDING
    FARMER, VC
    HAYES, NF
    THOMSON, RH
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1956, (SEP): : 3600 - 3607
  • [9] FISCHER C, 1904, BER, V37, P3220
  • [10] FRIDRICHSEN W, 1980, ADV HETEROCYCL CHEM, V26, P135