The directed lithiation of some 3-acylchromone acetals

被引:11
|
作者
Daia, GE
Gabbutt, CD [1 ]
Hepworth, JD
Heron, BM
Hibbs, DE
Hursthouse, MB
机构
[1] Univ Cent Lancashire, Dept Chem, Preston PR1 2HE, Lancs, England
[2] Univ Wales Coll Cardiff, Dept Chem, Cardiff CF1 3TB, S Glam, Wales
关键词
D O I
10.1016/S0040-4039(97)10733-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Acylchromone acetals are lithiated at C-2. Subsequent electrophilic trapping gives chromones 4 together with a ring-contracted dimer 6, During the formation of some acetals, an acid-catalysed rearrangement to a 2-substituted 3-formylchromone acetal is observed. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1215 / 1218
页数:4
相关论文
共 50 条
  • [41] Sulfoximine-Directed Arene ortho-Lithiation
    Gais, Hans-Joachim
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (46) : 6229 - 6246
  • [42] LITHIATION OF METHOXYPYRIDINES DIRECTED BY ALPHA-AMINO ALKOXIDES
    COMINS, DL
    KILLPACK, MO
    JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01): : 69 - 73
  • [43] RATE AND ORIENTATION EFFECT OF TMEDA ON DIRECTED LITHIATION REACTIONS
    SLOCUM, DW
    BOOK, G
    JENNINGS, CA
    TETRAHEDRON LETTERS, 1970, (39) : 3443 - &
  • [44] DIRECTED LITHIATION OF 1-TRIISOPROPYLSILYLGRAMINE - A SHORT ACCESS TO 3,4-DISUBSTITUTED INDOLES
    IWAO, M
    HETEROCYCLES, 1993, 36 (01) : 29 - 32
  • [45] Preparation of 3,4-enynoindoles via directed lithiation and application to the synthesis of 3,4-carbocycloindoles
    Perez-Serrano, L
    Casarrubios, L
    Domínguez, G
    Freire, G
    Pérez-Castells, J
    TETRAHEDRON, 2002, 58 (27) : 5407 - 5415
  • [46] The representation of some cyclic acetals
    Bersin, T
    Willfang, G
    BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1937, 70 : 2167 - 2173
  • [47] The conformation of some estrane acetals
    Yamamoto, C
    Matsumoto, T
    Matsumoto, T
    Watanabe, M
    Morais, G
    Mataka, S
    Thiemann, T
    JOURNAL OF CHEMICAL RESEARCH, 2005, (11) : 685 - 688
  • [48] SOME CYCLIC ACETALS OF GLYOXAL
    SPRUNG, MM
    GUENTHER, FO
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (04) : 1884 - 1886
  • [49] SOME RELATIONSHIPS OF DEALKOXYLATION OF ACETALS
    LEVIN, YM
    KATSNELSON, MG
    UZLYANERNEGLO, AL
    LEENSON, EI
    JOURNAL OF APPLIED CHEMISTRY OF THE USSR, 1980, 53 (01): : 148 - 151
  • [50] THE PREPARATION OF SOME CYCLIC ACETALS
    SULZBACHER, M
    BERGMANN, E
    PARISER, ER
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (08) : 2827 - 2828