Novel synthesis of furan-2-acetic esters by palladium-catalysed oxidative cyclization-alkoxycarbonylation of (Z)-2-En-4-yn-1-ols

被引：41
|
作者：
Gabriele, B [1 ]
Salerno, G [1 ]
DePascali, F [1 ]
Sciano, GT [1 ]
Costa, M [1 ]
Chiusoli, GP [1 ]
机构：
[1] UNIV PARMA,DIPARTIMENTO CHIM ORGAN & IND,I-43100 PARMA,ITALY
来源：
TETRAHEDRON LETTERS | 1997年 / 38卷 / 39期
关键词：
D O I：
10.1016/S0040-4039(97)01584-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Furan-2-acetic esters are obtained in good yields by direct oxidative cyclization-alkoxycarbonylation of (Z)-2-en-1-yn-1-ols. bearing both an alkyl or an aryl substituent alpha to the hydroxy group, in the presence of catalytic amounts of palladium iodide in conjunction with potassium iodide at 50-70 degrees C and 100 atm of a 9:1 mixture of carbon monoxide and air. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码：6877 / 6880
页数：4
相关论文
共 50 条
  • [1] An efficient and general synthesis of furan-2-acetic esters by palladium-catalyzed oxidative carbonylation of (Z)-2-en-4-yn-1-ols
    Gabriele, B
    Salerno, G
    De Pascali, F
    Costa, M
    Chiusoli, GP
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21): : 7693 - 7699
  • [2] Efficient and general synthesis of furan-2-acetic esters by palladium-catalyzed oxidative carbonylation of (Z)-2-en-4-yn-1-ols
    J Org Chem, 21 (7693-7699):
  • [3] A new and efficient synthesis of rosefuran. A general synthesis of furans by palladium-catalysed cycloisomerization of (Z)-2-en-4-yn-1-ols
    Gabriele, B
    Salerno, G
    CHEMICAL COMMUNICATIONS, 1997, (12) : 1083 - 1084
  • [4] SYNTHESIS OF FURANS BY CYCLIZATION OF 2-EN-4-YN-1-OLS IN THE PRESENCE OF RUTHENIUM AND PALLADIUM CATALYSTS
    SEILLER, B
    BRUNEAU, C
    DIXNEUF, PH
    TETRAHEDRON, 1995, 51 (47) : 13089 - 13102
  • [5] An easy and convenient synthesis of 2-furan-2-ylacetamides by sequential palladium-catalyzed oxidative aminocarbonylation of (Z)-2-En-4-yn-1-ols/conjugate addition/aromatization
    Gabriele, Bartolo
    Plastina, Pierluigi
    Salerno, Giuseppe
    Mancuso, Raffaella
    SYNTHESIS-STUTTGART, 2006, (24): : 4247 - 4251
  • [6] 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
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21): : 7687 - 7692
  • [7] Gold-catalyzed cyclization of (Z)-2-en-4-yn-1-ols:: Highly efficient synthesis of fully substituted dihydrofurans and furans
    Liu, YH
    Song, FJ
    Song, ZQ
    Liu, MN
    Yan, B
    ORGANIC LETTERS, 2005, 7 (24) : 5409 - 5412
  • [8] A general and efficient synthesis of substituted furans and dihydrofurans via gold-catalyzed cyclization of (Z)-2-en-4-yn-1-ols
    Du, Xiangwei
    Song, Feijie
    Lu, Yuhua
    Chen, Haoyi
    Liu, Yuanhong
    TETRAHEDRON, 2009, 65 (09) : 1839 - 1845
  • [9] Efficient Synthesis of Polysubstituted Furans through a Base-Promoted Oxacyclization of (Z)-2-En-4-yn-1-ols
    Hrizi, Asma
    Thiery, Emilie
    Romdhani-Younes, Moufida
    Jacquemin, Johan
    Thibonnet, Jerome
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (27) : 3798 - 3806
  • [10] SYNTHESIS OF BETA-ALLENIC ALCOHOLS BY REDUCTION OF 2-EN-4-YN-1-OLS .2.
    SANTELLI, M
    BERTRAND, M
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE PARTIE II-CHIMIE MOLECULAIRE ORGANIQUE ET BIOLOGIQUE, 1973, (7-8): : 2335 - 2340
12345