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 50 条
  • [31] Palladium-catalyzed enyne-yne [4+2] benzannulation as a new and general approach to polysubstituted benzenes
    Gevorgyan, V
    Yamamoto, Y
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) : 232 - 247
  • [32] PALLADIUM-CATALYZED COUPLING OF 2-BROMOANILINES WITH VINYLSTANNANES - A REGIOCONTROLLED SYNTHESIS OF SUBSTITUTED INDOLES
    KROLSKI, ME
    RENALDO, AF
    RUDISILL, DE
    STILLE, JK
    JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (06): : 1170 - 1176
  • [33] Synthesis of 2-Substituted Furans by Iron-and Palladium-Catalyzed Coupling Reactions
    Haner, Jamie
    Jack, Kelsey
    Nagireddy, Jaipal
    Raheem, Mohammed Abdul
    Durham, Robin
    Tam, William
    SYNTHESIS-STUTTGART, 2011, (05): : 731 - 738
  • [34] Novel palladium-catalyzed synthesis of 1,2-dihydro-4(3H)-carbazolones
    Scott, TL
    Söderberg, BCG
    TETRAHEDRON LETTERS, 2002, 43 (09) : 1621 - 1624
  • [35] Palladium-Catalyzed Tandem Synthesis of 2-Trifluoromethylthio(seleno)-Substituted Benzofused Heterocycles
    Zhang, Mengjia
    Weng, Zhiqiang
    ORGANIC LETTERS, 2019, 21 (15) : 5838 - 5842
  • [36] PALLADIUM-CATALYZED REACTIONS IN THE SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED INDOLES - APPROACHES TO ERGOT ALKALOIDS
    HARRINGTON, PJ
    HEGEDUS, LS
    JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (15): : 2657 - 2662
  • [37] SYNTHESIS OF DIHYDROBENZO [1,4] OXAZINES BY PALLADIUM-CATALYZED CYCLIZATION OF N-SUBSTITUTED 2-AMINOPHENOLS WITH PROPARGYLIC CARBONATES
    Yoshida, Masahiro
    Mori, Shunya
    Matsumoto, Kenji
    Hirokane, Tsukasa
    HETEROCYCLES, 2020, 101 (02) : 435 - 443
  • [38] Palladium-Catalyzed Cycloisomerization of (Z)-1-Iodo-1,6-dienes to 3-Aza-bicyclo[4.1.0]hept-2-enes
    Chi, Xiaochen
    Meng, Long
    Sun, Xi
    Liu, Qing
    Ai, Bing
    Chen, Lei
    Zhang, Daopeng
    Zhao, Pingping
    Dong, Yunhui
    Liu, Hui
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (06) : 840 - 843
  • [39] AN EFFICIENT PALLADIUM-CATALYZED STEREOCONTROLLED SYNTHESIS OF 4A-ANGULAR METHYL-SUBSTITUTED HYDROFLUORENES
    MUKHOPADHYAYA, JK
    PAL, S
    GHATAK, UR
    SYNTHETIC COMMUNICATIONS, 1995, 25 (11) : 1641 - 1657
  • [40] Novel and convenient synthesis of substituted quinolines by copper- or palladium-catalyzed cyclodehydration of 1-(2-aminoaryl)-2-yn-1-ols
    Gabriele, Bartolo
    Mancuso, Raffaella
    Salerno, Giuseppe
    Ruffolo, Giuseppe
    Plastina, Pierluigi
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (18): : 6873 - 6877