Selective synthesis of 3-methyleneindolin-2-ones by one-pot multicatalytic processes

被引：26
作者：
Song, Ren-Jie [1 ]
Liu, Yu [1 ]
Li, Rong-Jiang [1 ]
Li, Jin-Heng [1 ]
机构：
[1] Hunan Normal Univ, Minist Educ, Key Lab Chem Biol & Tradit Chinese Med Res, Changsha 410081, Hunan, Peoples R China
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 27期
基金：
中国国家自然科学基金;
关键词：
Copper; Palladium; Amination; C-H functionalization; Propiolamide; 3-Methyleneindolin-2-one; EFFICIENT COPPER CATALYST; GROWTH-FACTOR RECEPTOR; C-H FUNCTIONALIZATION; ARYL HALIDES; STEREOSELECTIVE-SYNTHESIS; DOMINO REACTIONS; TYROSINE KINASE; AMIDATION; TANDEM; DISCOVERY;
D O I：
10.1016/j.tetlet.2009.04.066
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel one-pot multicatalytic route for the synthesis of 3-methyleneindolin-2-ones has been developed involving sequential copper-catalyzed amination and palladium-catalyzed C-H functionalization processes. In the presence of CuI and Pd(OAc)(2), a variety of propiolamides underwent the reaction with iodides to afford the corresponding 3-methyleneindolin-2-ones in moderate yields. (c) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3912 / 3916
页数：5
相关论文
共 63 条
[41]   Synthesis of enamides related to the salicylate antitumor macrolides using copper-mediated vinylic substitution [J].
Shen, RC ;
Porco, JA .
ORGANIC LETTERS, 2000, 2 (09) :1333-1336
[42]   Rhodium-catalyzed multicomponent-coupling reactions involving a carborhodation-cross-coupling sequence [J].
Shintani, Ryo ;
Yamagami, Takafumi ;
Hayashi, Tamio .
ORGANIC LETTERS, 2006, 8 (21) :4799-4801
[43]   Discovery of 5-[5-Fluoro-2-oxo-1,2-dihydroindol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide, a novel tyrosine kinase inhibitor targeting vascular endothelial and platelet-derived growth factor receptor tyrosine kinase [J].
Sun, L ;
Liang, C ;
Shirazian, S ;
Zhou, Y ;
Miller, T ;
Cui, J ;
Fukuda, JY ;
Chu, JY ;
Nematalla, A ;
Wang, XY ;
Chen, H ;
Sistla, A ;
Luu, TC ;
Tang, F ;
Wei, J ;
Tang, C .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (07) :1116-1119
[44]   Design, synthesis, and evaluations of substituted 3-[(3-or 4-carboxyethylpyrrol-2-yl)methylidenyl]indolin-2-ones as inhibitors of VEGF, FGF, and PDGF receptor tyrosine kinases [J].
Sun, L ;
Tran, N ;
Liang, CX ;
Tang, F ;
Rice, A ;
Schreck, R ;
Waltz, K ;
Shawver, LK ;
McMahon, G ;
Tang, C .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (25) :5120-5130
[45]   Palladium-catalyzed C-H functionalization of N-arylpropiolamides with aryliodonium salts:: Selective synthesis of 3-(1-arylmethylene)oxindoles [J].
Tang, Shi ;
Peng, Peng ;
Zhong, Ping ;
Li, Jin-Heng .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14) :5476-5480
[46]   Synthesis of (2-oxoindolin-3-ylidene)methyl acetates involving a C-H functionalization process [J].
Tang, Shi ;
Peng, Peng ;
Wang, Zhi-Qiang ;
Tang, Bo-Xiao ;
Deng, Chen-Liang ;
Li, Jin-Heng ;
Zhong, Ping ;
Wang, Nai-Xing .
ORGANIC LETTERS, 2008, 10 (09) :1875-1878
[47]   Sequential intermolecular aminopalladation/ortho-arene C-H activation reactions of N-phenylpropiolamides with phthalimide [J].
Tang, Shi ;
Peng, Peng ;
Pi, Shao-Feng ;
Liang, Yun ;
Wang, Nai-Xing ;
Li, Jin-Heng .
ORGANIC LETTERS, 2008, 10 (06) :1179-1182
[48]   Palladium-catalyzed carbonylative annulation reaction of 2-(1-alkynyl)benzenamines: Selective synthesis of 3-(Halomethylene)indolin-2-ones [J].
Tang, Shi ;
Yu, Quan-Fu ;
Peng, Peng ;
Li, Jin-Heng ;
Zhong, Ping ;
Tang, Ri-Yuan .
ORGANIC LETTERS, 2007, 9 (17) :3413-3416
[49]   Co-operative effect of Lewis acids with transition metals for organic synthesis [J].
Wang, Congyang ;
Xi, Zhenfeng .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (09) :1395-1406
[50]   Photoreactions of 1-acetylisatin with alkynes:: Regioselectivity in oxetene formation and easy access to 3-alkylideneoxindoles and dispiro[oxindole[3,2′]furan[3′,3′′]oxindole]s [J].
Wang, L ;
Zhang, Y ;
Hu, HY ;
Fun, HK ;
Xu, JH .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :3850-3858
1234567