Palladium-Catalyzed Cyclocarbonylation of 2-Halobenzaldehyde and Hydrazines: A Facile Synthesis of 2-Aminoisoindolin-1-ones

被引:5
作者
Han, Chao [1 ]
Shen, Yang [1 ]
Lu, Ping [1 ]
Wang, Yanguang [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
cyclocarbonylation; 2-aminoisoindolin-1-ones; multicomponent reactions; heterocycles; CARBONYLATIVE CYCLIZATION; DOMINO REACTION; MULTICOMPONENT REACTIONS; 2-IODOBENZOYL CHLORIDE; AMINES; 2-BROMOBENZALDEHYDE; STAUROSPORINE; ALDEHYDES; SEQUENCE; INDOLES;
D O I
10.1002/cjoc.201200798
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient procedure for the synthesis of 2-aminoisoindolin-1-ones via a palladium-catalyzed three-component reaction of 2-halobenzaldehydes, hydrazines and carbon monoxide is reported. This cyclocarbonylation process can be performed smoothly under 1 atmospheric pressure of carbon monoxide to afford 2-aminoisoindolin-1-ones in moderate to excellent yields.
引用
收藏
页码:182 / 186
页数:5
相关论文
共 43 条
[1]   Mechanistic Variations of the Povarov Multicomponent Reaction and Related Processes [J].
Bello, Davide ;
Ramon, Rosario ;
Lavilla, Rodolfo .
CURRENT ORGANIC CHEMISTRY, 2010, 14 (04) :332-356
[2]   A new and efficient palladium-catalyzed synthesis of a 2,3,4,5-tetrahydro-1H-2,4-benzodiazepine-1,3-dione derivative [J].
Bocelli, G ;
Catellani, M ;
Cugini, F ;
Ferraccioli, R .
TETRAHEDRON LETTERS, 1999, 40 (13) :2623-2624
[3]   Syntheses of Substituted 3-Methyleneisoindolin-1-ones By a Palladium-Catalyzed Sonogashira Coupling-Carbonylation-Hydroamination Sequence in Phosphonium Salt-Based Ionic liquids [J].
Cao, Hong ;
McNamee, Laura ;
Alper, Howard .
ORGANIC LETTERS, 2008, 10 (22) :5281-5284
[4]   Synthesis of Unsaturated Seven-Membered Ring Lactams through Palladium-Catalyzed Amination and Intramolecular Cyclocarbonylation Reactions of Amines and Baylis-Hillman Acetates [J].
Cao, Hong ;
Vieira, Tiago O. ;
Alper, Howard .
ORGANIC LETTERS, 2011, 13 (01) :11-13
[5]   Synthesis of alkyl 2,5-dihydro-5-oxofuran-2-carboxylates via palladium-catalyzed carbonylative cyclization of β-bromovinyl aldehydes in alcohols [J].
Cho, Chan Sik ;
Kim, Jun Uk ;
Choi, Heung-Jin .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (24) :3677-3680
[6]   Palladium-catalyzed carbonylative cyclization of 2-bromobenzaldehyde with primary amines leading to isoindolin-1-ones [J].
Cho, Chan Sik ;
Ren, Wen Xiu .
TETRAHEDRON LETTERS, 2009, 50 (18) :2097-2099
[7]   Palladium-catalyzed diastereoselective synthesis of isoindolinones [J].
Cho, CS ;
Chu, DY ;
Lee, DY ;
Shim, SC ;
Kim, TJ ;
Lim, WT ;
Heo, NH .
SYNTHETIC COMMUNICATIONS, 1997, 27 (23) :4141-4158
[8]   Synthesis of 3-alkenylisoindolin-1-ones via palladium(O)-catalyzed coupling and cyclization between 2-iodobenzoyl chloride and aldimines [J].
Cho, CS ;
Wu, X ;
Jiang, LH ;
Shim, SC ;
Choi, HJ ;
Kim, TJ .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, 35 (01) :265-268
[9]   Palladium-catalyzed synthesis of 3-(alkylamino)isoindolin-1-ones by carbonylative cyclization of 2-bromobenzaldehyde with primary amines [J].
Cho, CS ;
Jiang, LH ;
Lee, DY ;
Shim, SC ;
Lee, HS ;
Cho, SD .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (04) :1371-1374
[10]   Synthesis of spiroisoindolinones by palladium-catalyzed heterocyclization of 2-iodobenzoyl chloride with ketimines [J].
Cho, CS ;
Wu, X ;
Jiang, LH ;
Shim, SC ;
Kim, HR .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (01) :297-300