Palladium-Catalyzed Cyclization/Carbonylation as a Direct Route to 4-[(Methoxycarbonyl)methyl]-3,4-dihydroisoquinolinones

被引:8
作者
Ardizzoia, G. Attilio [1 ]
Beccalli, Egle M. [2 ]
Borsini, Elena [1 ]
Brenna, Stefano [1 ]
Broggini, Gianluigi [1 ]
Rigamonti, Micol [1 ]
机构
[1] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy
[2] Univ Milan, Fac Farm, Ist Chim Organ A Marchesini, I-20133 Milan, Italy
关键词
Carbonylations; Cyclizations; Palladium; Nitrogen heterocycles;
D O I
10.1002/ejoc.200800747
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthetic protocol for the preparation of 4-[(methoxycarbonyl)methyl]-3,4-dihydroisoquinolin-1-ones from N-allylamides of 2-iodobenzoic acids has been performed under 100 atm of carbon monoxide. Pyridine ring formation occurs through an intramolecular Pd-catalyzed carbon-carbon bond formation, followed by an alkoxycarbonylation process. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
引用
收藏
页码:5590 / 5596
页数:7
相关论文
共 54 条
[51]  
Vizer SA, 2004, TETRAHEDRON, V60, P5499, DOI 10.1016/j.tet.2004.04.046
[52]   Intramolecular palladium(II)-mediated alkoxy carbonylation as a route to functionalized tetrahydropyrans. Synthesis of the C9-C32 segment of phorboxazole A [J].
White, JD ;
Kranemann, CL ;
Kuntiyong, P .
ORGANIC LETTERS, 2001, 3 (25) :4003-4006
[53]   PALLADIUM-CATALYZED CARBONYLATIVE CYCLIZATION OF ORTHO-ALLYLBENZYL HALIDES TO PRODUCE BENZO-ANNULATED ENOL LACTONES AND OR BICYCLO[3.3.0]HEPT-3-EN-6-ONES - AN EFFICIENT ROUTE TO U-68,215 [J].
WU, GZ ;
SHIMOYAMA, I ;
NEGISHI, E .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) :6506-6507
[54]   Ionic-liquid-promoted palladium-catalyzed multicomponent cyclocarbonylation of o-iodoanilines and allenes to form methylene-2,3-dihydro-1H-quinolin-4-ones [J].
Ye, Fangguo ;
Alper, Howard .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (09) :3218-3222