Sequential reaction of carbon dioxide and carbon monoxide with acetylenic amines in the presence of a palladium catalyst

被引:39
作者
Chiusoli, GP
Costa, M
Gabriele, B
Salerno, G
机构
[1] Univ Parma, Dipartimento Chim Organ & Ind, I-43100 Parma, Italy
[2] Univ Calabria, Dipartimento Chim, I-87030 Cosenza, Italy
关键词
carbon dioxide; carbon monoxide; acetylenic amines; palladium catalyst; (alkoxycarbonyl)methyleneoxazolidinones;
D O I
10.1016/S1381-1169(98)00397-5
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Conditions for the sequential reaction of carbon dioxide with an acetylenic amine and carbon monoxide in the presence of a PdI2-KI catalyst in alcohols are examined. The stereochemistry of the two 5-(alkoxycarbonyl)methylene-3,4,4-trialkyl-1,3-oxazolidin-2-one stereoisomers obtained is attributed to different pathways on the basis of experiments carried out on alkyl and benzyl esters of N-alkyldimethylpropynylcarbamic acid and carbon monoxide. (C) 1999 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:297 / 310
页数:14
相关论文
共 15 条
[1]   Palladium-catalysed sequential carboxylation-alkoxycarbonylation of acetylenic amines [J].
Bacchi, A ;
Chiusoli, GP ;
Costa, M ;
Gabriele, B ;
Righi, C ;
Salerno, G .
CHEMICAL COMMUNICATIONS, 1997, (13) :1209-1210
[2]   Nitrogen heterocycles by palladium-catalysed oxidative cyclization-alkoxycarbonylation of acetylenic ureas [J].
Bacchi, A ;
Chiusoli, GP ;
Costa, M ;
Sani, C ;
Gabriele, B ;
Salerno, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 562 (01) :35-43
[3]   VERSATILE SYNTHESIS OF BETA-LACTAMS, GAMMA-LACTAMS OR OXAZOLINES BY PALLADIUM-CATALYSED OXIDATIVE CARBONYLATION OF 1-SUBSTITUTED PROP-2-YNYLAMINES [J].
BONARDI, A ;
COSTA, M ;
GABRIELE, B ;
SALERNO, G ;
CHIUSOLI, GP .
TETRAHEDRON LETTERS, 1995, 36 (41) :7495-7498
[4]   SYNTHESIS AND X-RAY STRUCTURE OF THE NICKELABENZOCYCLOPENTENE COMPLEX (ME3P)2NI(CH2CME2-ORTHO-C6H4) - REACTIVITY TOWARD SIMPLE, UNSATURATED MOLECULES AND THE CRYSTAL AND MOLECULAR-STRUCTURE OF THE CYCLIC CARBOXYLATE (ME3P)2NI(CH2CME2-ORTHO-C6H4C(O)O) [J].
CARMONA, E ;
GUTIERREZPUEBLA, E ;
MARIN, JM ;
MONGE, A ;
PANEQUE, M ;
POVEDA, ML ;
RUIZ, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) :2883-2891
[5]  
Carter H. E., 1955, ORGANIC SYNTHESIS CO, V3, P167
[6]   Superbase catalysis of oxazolidin-2-one ring formation from carbon dioxide and prop-2-yn-1-amines under homogeneous or heterogenous conditions [J].
Costa, M ;
Chiusoli, GP ;
Taffurelli, D ;
Dalmonego, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (09) :1541-1546
[7]   Base-catalysed direct introduction of carbon dioxide into acetylenic amines [J].
Costa, M ;
Chiusoli, GP ;
Rizzardi, M .
CHEMICAL COMMUNICATIONS, 1996, (14) :1699-1700
[8]   A simple catalytic system for the substitutive carbonylation of allyl alcohols to beta,gamma-unsaturated acids or esters [J].
Gabriele, B ;
Salerno, G ;
Costa, M ;
Chiusoli, GP .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1996, 111 (1-2) :43-48
[9]   AN EFFICIENT AND SELECTIVE PALLADIUM-CATALYZED OXIDATIVE DICARBONYLATION OF ALKYNES TO ALKYL-MALEIC OR ARYL-MALEIC ESTERS [J].
GABRIELE, B ;
COSTA, M ;
SALERNO, G ;
CHIUSOLI, GP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (01) :83-87
[10]   COPPER(I)-CATALYZED AMINATION OF PROPARGYL ESTERS - SELECTIVE SYNTHESIS OF PROPARGYLAMINES, 1-ALKEN-3-YLAMINES, AND (Z)-ALLYLAMINES [J].
IMADA, Y ;
YUASA, M ;
NAKAMURA, I ;
MURAHASHI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2282-2284