Novel synthesis of substituted thiophenes by palladium-catalyzed cycloisomerization of (Z)-2-en-4-yne-1-thiols

被引:72
作者
Gabriele, B [1 ]
Salerno, G [1 ]
Fazio, A [1 ]
机构
[1] Univ Calabria, Dipartimento Chim, I-87030 Cosenza, Italy
关键词
D O I
10.1021/ol991297c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The first example of palladium-catalyzed cycloisomerization of (Z)-2-en-4-yne-1-thiols 1 to give substituted thiophenes 2 is reported. Cycloisomerization reactions are carried out under nitrogen at 25-100 degrees C in N,N-dimethylacetamide as the solvent in the presence of catalytic amounts of Pdl(2) in conjunction with Kl to give the corresponding thiophenes in 43-94% yield.
引用
收藏
页码:351 / 352
页数:2
相关论文
共 25 条
  • [1] Bertram H. J., 1993, RECENT DEV FLAVOR FR
  • [2] COPPOLA GM, 1995, SYNLETT, P1143
  • [3] EICHINGER K, 1989, SYNTHESIS-STUTTGART, P210
  • [4] Synthesis of 3,4-bis[(methoxycarbonyl)methyl]thiophene and bis-, ter- and and pentathiophenes with alternating 3,4-bis[(methoxycarbonyl)methyl]-substituted rings
    Fazio, A
    Gabriele, B
    Salerno, G
    Destri, S
    [J]. TETRAHEDRON, 1999, 55 (02) : 485 - 502
  • [5] A general and facile synthesis of substituted furans by palladium-catalyzed cycloisomerization of (Z)-2-En-4-yn-1-ols
    Gabriele, B
    Salerno, G
    Lauria, E
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) : 7687 - 7692
  • [6] Synthesis of aromatic heterocycles
    Gilchrist, TL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (20): : 2849 - 2866
  • [7] Synthesis of aromatic heterocycles
    Gilchrist, TL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (03): : 615 - 628
  • [8] Gronowitz S., 1991, CHEM HETEROCYCLIC CO, V44
  • [9] Guan HP, 1997, SYNTHESIS-STUTTGART, P461
  • [10] Regioselective syntheses of substituted furans
    Hou, XL
    Cheung, HY
    Hon, TY
    Kwan, PL
    Lo, TH
    Tong, SY
    Wong, HNC
    [J]. TETRAHEDRON, 1998, 54 (10) : 1955 - 2020