Synthesis of polyfunctionalized thiophenes and enediynes via ring-opening reactions of 3-lithiated thieno[2,3-b](and [3,2-b])thiophenes, 3,4-dilithiated thieno[2,3-b]thiophenes and 3,6-dilithiated thieno[3,2-b]thiophenes

被引：13
|
作者：
Fuller, LS
Iddon, B
Smith, KA
机构：
[1] Synthet Chem Ltd, Wolverhampton WV10 7BP, England
[2] Univ Salford, Sci Res Inst, Div Chem Sci, Salford M5 4WT, Lancs, England
来源：
CHEMICAL COMMUNICATIONS | 1997年 / 24期
关键词：
D O I：
10.1039/a707033k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Solutions of the title lithiated thienothiophenes were synthesized from 2,5-disubstituted 3,4-dibromothieno[2,3-b]thiophenes or 3,6-dibromothieno[3,2-b]thiophenes via Br --> Li exchange with 1.0 or 2.0 equiv. of BuLi (THF, -78 degrees C), respectively, and gave either polyfunctionalized thiophenes or polyfunctionalized enediynes (by a novel tandem ring-opening process in these cases) on being allowed to warm up to ambient temperature.
引用
收藏
页码：2355 / 2356
页数：2
相关论文
共 50 条
  • [21] 3-AMINO-THIENO[2,3-B]FURANS AND 3-AMINO-THIENO[3,2-B]FURANS
    GEWALD, K
    BELLMANN, P
    JOURNAL FUR PRAKTISCHE CHEMIE, 1983, 325 (03): : 457 - 462
  • [22] A convenient synthesis of 2,3,4,5-functionalised thieno[2,3-b]thiophenes
    Sommen, Geoffroy
    Comel, Alain
    Kirsch, Gilbert
    Synthesis, 2003, (05) : 735 - 741
  • [23] ELECTROPHILIC SUBSTITUTION OF THIENO[2,3-B]THIOPHENE AND THIENO[3,2-B]THIOPHENE - QUANTITATIVE STUDY
    BUGGE, A
    CHEMICA SCRIPTA, 1972, 2 (03): : 137 - &
  • [24] MASS-SPECTRA OF ISOMERIC THIENO[2,3-B]PYRIDINES AND THIENO[3,2-B]PYRIDINES
    KLYUYEV, NA
    ABRAMENKO, PI
    SHPILEVA, IS
    PINKIN, LD
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1982, (06): : 757 - 761
  • [25] A convenient synthesis of 2,3,4,5-functionalised thieno[2,3-b]thiophenes
    Sommen, G
    Comel, A
    Kirsch, G
    SYNTHESIS-STUTTGART, 2003, (05): : 735 - 741
  • [26] THIENO[2,3-B]PYRIDINES AND THIENO[3,2-B]PYRIDINES BY METHOD OF GOULD-JACOBS
    KHAN, MA
    GUARCONI, AE
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1977, 14 (05) : 807 - 812
  • [27] THIENO[2,3-B][1]BENZOTHIOPHEN AND THIENO[3,2-B][1]BENZOTHIOPHEN .2. SUBSTITUTION REACTIONS
    CHAPMAN, NB
    HUGHES, CG
    SCROWSTO.RM
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (03): : 463 - &
  • [28] Palladium-Catalyzed C-S Coupling: Access to Thioethers, Benzo[b]thiophenes, and Thieno[3,2-b]thiophenes
    Kuhn, Marius
    Falk, Florian C.
    Paradies, Jan
    ORGANIC LETTERS, 2011, 13 (15) : 4100 - 4103
  • [29] IMPROVED SYNTHESES OF THIENO[2,3-B]-FUSED AND [3,2-B]-FUSED NAPHTHYRIDINES
    BJORK, P
    AAKERMANN, T
    HORNFELDT, AB
    GRONOWITZ, S
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (03) : 751 - 754
  • [30] METALATION OF THIENO[2,3-B]THIOPHENE AND THIEN/(3,2-B]THIOPHENE WITH BUTYLLITHIUM
    BUGGE, A
    ACTA CHEMICA SCANDINAVICA, 1968, 22 (01): : 63 - &
12345