Pd(II)-Catalyzed Synthesis of Carbolines by Iminoannulation of Internal Alkynes via Direct C-H Bond Cleavage Using Dioxygen as Oxidant

被引:127
作者
Ding, Shengtao [1 ]
Shi, Zhuangzhi [1 ]
Jiao, Ning [1 ,2 ]
机构
[1] Peking Univ, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
[2] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
美国国家科学基金会;
关键词
PALLADIUM-CATALYZED IMINOANNULATION; ANNULATED GAMMA-CARBOLINES; BETA-CARBOLINE; MOLECULAR-OXYGEN; ORGANIC-CHEMICALS; A-C; ALKALOIDS; DERIVATIVES; INDOLES; FUNCTIONALIZATION;
D O I
10.1021/ol100272s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed iminoannulation of Internal alkynes via direct C-H bond cleavage was developed. Dioxygen was employed as a clean oxidant In this kind of catalysis. Carbolines were synthesized from tert-butylimines of N-substituted Indole-2-carboxaldehydes or indole-3-carboxaldehydes.
引用
收藏
页码:1540 / 1543
页数:4
相关论文
共 72 条
[1]   γ-Carbolines and their hydrogenated derivatives. 1. Aromatic γ-carbolines: methods of synthesis, chemical and biological properties (review) [J].
Alekseyev, R. S. ;
Kurkin, A. V. ;
Yurovskaya, M. A. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (08) :889-925
[2]  
BATANOVA OV, 2004, TETRAHEDRON LETT, V45, P1299
[3]   Nostocarboline:: Isolation and synthesis of a new cholinesterase inhibitor from Nostoc 78-12A [J].
Becher, PG ;
Beuchat, J ;
Gademann, K ;
Jüttner, F .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (12) :1793-1795
[4]   Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: Regioselective and switchable C-H alkenylation and annulation of pyrroles [J].
Beck, EM ;
Grimster, NP ;
Hatley, R ;
Gaunt, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2528-2529
[5]   Synthesis and structure-activity relationships of γ-carboline derivatives as potent and selective cysLT1 antagonists [J].
Bonjoch, Josep ;
Diaba, Faiza ;
Pages, Lluis ;
Perez, Daniel ;
Soca, Lidia ;
Miralpeix, Montserrat ;
Vilella, Dolors ;
Anton, Paquita ;
Puig, Carles .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (15) :4299-4302
[6]   Simple synthesis of γ-carbolines [J].
Butin, A. V. ;
Pilipenko, A. S. ;
Milich, A. A. ;
Finko, A. V. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (05) :613-614
[7]   Synthesis and cytotoxic activities of 1-benzylidine substituted β-carboline derivatives [J].
Cao, Rihui ;
Yi, Wei ;
Wu, Qifeng ;
Guan, Xiangdong ;
Feng, Manxiu ;
Ma, Chunming ;
Chen, Zhiyong ;
Song, Huacan ;
Peng, Wenlie .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (24) :6558-6561
[8]   Catalytic Sequential Reactions Involving Palladacycle-Directed Aryl Coupling Steps [J].
Catellani, Marta ;
Motti, Elena ;
Della Ca, Nicola .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1512-1522
[9]   Fe-catalyzed highly selective ring expansion of alkynylcyclopropyl alkanols to cyclobutanols [J].
Chen, Anjun ;
Lin, Riyuan ;
Liu, Qingjian ;
Jiao, Ning .
CHEMICAL COMMUNICATIONS, 2009, (44) :6842-6844
[10]   Design, synthesis, and quantitative structure-activity relationship of cytotoxic γ-carboline derivatives [J].
Chen, Jing ;
Dong, Xiaowu ;
Liu, Tao ;
Lou, Jianshu ;
Jiang, Chaoyi ;
Huang, Wenhai ;
He, Qiaojun ;
Yang, Bo ;
Hua, Yongzhou .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (09) :3324-3331