Synthesis of 3-(aminomethylene)-2-oxoindolines by palladium-catalyzed annulation of 3-chloro-2-iodo-N-arylacrylamides with amides or amines

被引:8
作者
Deng, Guo-Bo [2 ]
Wang, Zhi-Qiang [2 ]
Song, Ren-Jie [2 ]
Zhou, Ming-Bo [2 ]
Wei, Wen-Ting [2 ]
Xie, Peng [2 ]
Li, Jin-Heng [1 ]
机构
[1] Hunan Univ, State Key Lab Chemo Biosensing & Chemometr, Coll Chem & Chem Engn, Changsha 410082, Hunan, Peoples R China
[2] Hunan Normal Univ, Key Lab Chem Biol & Tradit Chinese Med Res, Minist Educ, Changsha 410081, Hunan, Peoples R China
关键词
C-H FUNCTIONALIZATION; STEREOSELECTIVE-SYNTHESIS; CYCLIZATION REACTION; OXINDOLE SYNTHESIS; 2-(ALKYNYL)ARYL ISOCYANATES; 2-ALKYNYLARYL ISOCYANATES; BOND FUNCTIONALIZATION; SELECTIVE SYNTHESIS; KINASE INHIBITORS; DIRECT ARYLATION;
D O I
10.1039/c1cc11602a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new palladium-catalyzed C-H bond activation-annulation-amination tandem method was presented for selectively synthesizing 3-(aminomethylene)-2-oxoindolines. In the presence of Pd(dba)(2), xantphos (L8), AgOAc and Na2CO3, a variety of 3-chloro-2-iodo-N-arylacrylamides underwent the reaction with amides or amines to afford the corresponding 3-(aminomethylene)2-oxoindolines in moderate to good yields.
引用
收藏
页码:8151 / 8153
页数:3
相关论文
共 59 条
[1]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[2]   Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions [J].
Campeau, LC ;
Parisien, M ;
Jean, A ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) :581-590
[3]   Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules [J].
Campeau, LC ;
Fagnou, K .
CHEMICAL COMMUNICATIONS, 2006, (12) :1253-1264
[4]   A tandem Heck-carbocyclization/Suzuki-coupling approach to the stereoselective syntheses of asymmetric 3,3-(diarylmethylene)indolinones [J].
Cheung, WS ;
Patch, RJ ;
Player, MR .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3741-3744
[5]   Heck-Suzuki-Miyaura domino reactions involving ynamides.: An efficient access to 3-(Arylmethylene)isoindolinones [J].
Couty, S ;
Liégault, B ;
Meyer, C ;
Cossy, J .
ORGANIC LETTERS, 2004, 6 (15) :2511-2514
[6]   A domino sequence consisting of insertion, coupling, isomerization, and Diels-Alder steps yields highly fluorescent spirocycles [J].
D'Souza, DM ;
Rominger, F ;
Müller, TJJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (01) :153-158
[7]   Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds [J].
Daugulis, Olafs ;
Do, Hien-Quang ;
Shabashov, Dmitry .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) :1074-1086
[8]  
Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO
[9]  
2-6
[10]   Intramolecular carbolithiation of alkynes:: anti selectivity [J].
Fressigne, Catherine ;
Girard, Anne-Lise ;
Durandetti, Muriel ;
Maddaluno, Jacques .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (05) :891-893