2-substituted-3-allenyl-benzo[b]furans through the palladium-catalysed cyclization of propargylic o-(alkynyl)phenyl ethers.

被引:114
作者
Cacchi, S [1 ]
Fabrizi, G [1 ]
Moro, L [1 ]
机构
[1] Univ La Sapienza, Dipartimento Studi Chim & Tecnol Sostanze Biol At, I-00185 Rome, Italy
关键词
D O I
10.1016/S0040-4039(98)00936-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of propargylic o-(alkynyl)phenyl ethers in the presence of' Pd(PPh3)(4) and K2CO3 affords 2-substituted-3-allenylbenzo [b] furans in good yields. Depending on the nature of the starting alkyne, variable amounts of isomeric 2-substituted-3-propargylbenzo[b]furans have bren isolated. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5101 / 5104
页数:4
相关论文
共 15 条
[1]   THE PALLADIUM-CATALYZED SYNTHESIS OF 2,3,5-TRISUBSTITUTED FURANS FROM 2-PROPARGYL-1,3-DICARBONYL COMPOUNDS AND VINYLIC OR ARYL TRIFLATES OR HALIDES [J].
ARCADI, A ;
CACCHI, S ;
LAROCK, RC ;
MARINELLI, F .
TETRAHEDRON LETTERS, 1993, 34 (17) :2813-2816
[2]   A palladium-catalyzed domino reaction of 3-acetyl-5-hexyn-2-one with aryl iodides under carbon monoxide [J].
Arcadi, A ;
Rossi, E .
TETRAHEDRON LETTERS, 1996, 37 (37) :6811-6814
[3]  
Arcadi A, 1997, SYNLETT, P1315
[4]   2-SUBSTITUTED-3-ACYLINDOLES THROUGH THE PALLADIUM-CATALYZED CARBONYLATIVE CYCLIZATION OF 2-ALKYNYLTRIFLUOROACETANILIDES WITH ARYL HALIDES AND VINYL TRIFLATES [J].
ARCADI, A ;
CACCHI, S ;
CARNICELLI, V ;
MARINELLI, F .
TETRAHEDRON, 1994, 50 (02) :437-452
[5]  
Arcadi A, 1997, SYNLETT, P941
[6]   Palladium-catalyzed reaction of o-ethynylphenols, o-((trimethylsilyl)ethynyl)phenyl acetates, and o-alkynylphenols with unsaturated triflates or halides: A route to 2-substituted-, 2,3-disubstituted-, and 2-substituted-3-acylbenzo[b]furans [J].
Arcadi, A ;
Cacchi, S ;
DelRosario, M ;
Fabrizi, G ;
Marinelli, F .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9280-9288
[7]   TOTAL SYNTHESIS OF THE TRIQUINANE MARINE SESQUITERPENE (PLUS-OR-MINUS)DELTA(9(12)) CAPNELLENE USING A PALLADIUM-CATALYZED BIS-CYCLIZATION STEP [J].
BALME, G ;
BOUYSSI, D .
TETRAHEDRON, 1994, 50 (02) :403-414
[8]   PALLADIUM-CATALYZED SYNTHESIS OF NEW UNSATURATED EXO-ENOL LACTONES WITH POTENTIAL BIOLOGICAL-ACTIVITY [J].
BOUYSSI, D ;
GORE, J ;
BALME, G ;
LOUIS, D ;
WALLACH, J .
TETRAHEDRON LETTERS, 1993, 34 (19) :3129-3130
[9]  
Bouyssi D, 1997, SYNLETT, P944
[10]  
Cacchi S, 1997, SYNLETT, P1363