Base promoted reactions of 4-pentynones.

被引:29
作者
Arcadi, A [1 ]
Marinelli, F [1 ]
Pini, E [1 ]
Rossi, E [1 ]
机构
[1] UNIV MILAN,FAC FARM,IST CHIM ORGAN,I-20139 MILAN,ITALY
关键词
D O I
10.1016/0040-4039(96)00553-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Different substituted furans are syntetised by cyclization of 4-pentynones using potassium tert-butoxide in DMF. A different reaction pattern is observed when the same compounds were treated with sodium methoxide in MeOH. A new approach to 2-propargyl-carbonyl compounds is also proposed. (C) 1996 Elsevier Science Ltd
引用
收藏
页码:3387 / 3390
页数:4
相关论文
共 11 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]  
ARCADI A, 1992, CHEM LETT, P2479
[3]  
BARLUENGA J, 1990, SYNLETT, P673
[4]   A NEW PATHWAY TO ALKYNYL KETONES VIA PALLADIUM-CATALYZED CARBONYLATIVE COUPLING OF VINYL TRIFLATES WITH 1-ALKYNES [J].
CIATTINI, PG ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1991, 32 (44) :6449-6452
[5]   A NOVEL FURAN RING CONSTRUCTION AND SYNTHESES OF 4-SUBSTITUTED AND 4,5-SUBSTITUTED 2-(ALPHA-HETEROCYCLOALKYL)FURANS [J].
KATRITZKY, AR ;
LI, JQ .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (03) :638-643
[6]  
KLUGE AF, 1971, J ORG CHEM, V36, P1977
[7]   SYNTHESIS OF THE PSEUDOPTERANE AND FURANOCEMBRANE RING-SYSTEMS BY INTRAANNULAR CYCLIZATION OF BETA-ALKYNYL AND GAMMA-ALKYNYL ALLYLIC ALCOHOLS [J].
MARSHALL, JA ;
DUBAY, WJ .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (07) :1703-1708
[8]  
OSTENSEN ET, 1976, ACTA CHEM SCAND B, V30, P635, DOI 10.3891/acta.chem.scand.30b-0635
[9]   PALLADIUM-MEDIATED AND/OR COPPER-MEDIATED CROSS-COUPLING REACTIONS BETWEEN 1-ALKYNES AND VINYL, ARYL, 1-ALKYNYL, 1,2-PROPADIENYL, PROPARGYL AND ALLYLIC HALIDES OR RELATED-COMPOUNDS - A REVIEW [J].
ROSSI, R ;
CARPITA, A ;
BELLINA, F .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1995, 27 (02) :127-160
[10]   ENAMINE ALKYLATION AND ACYLATION OF CARBONYL COMPOUNDS [J].
STORK, G ;
SZMUSZKOVICZ, J ;
TERRELL, R ;
BRIZZOLARA, A ;
LANDESMAN, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (02) :207-&