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 [J].
Fazio, A ;
Gabriele, B ;
Salerno, G ;
Destri, S .
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 [J].
Gabriele, B ;
Salerno, G ;
Lauria, E .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :7687-7692
[6]   Synthesis of aromatic heterocycles [J].
Gilchrist, TL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (20) :2849-2866
[7]   Synthesis of aromatic heterocycles [J].
Gilchrist, TL .
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 [J].
Hou, XL ;
Cheung, HY ;
Hon, TY ;
Kwan, PL ;
Lo, TH ;
Tong, SY ;
Wong, HNC .
TETRAHEDRON, 1998, 54 (10) :1955-2020