Palladium-catalyzed oxidative carbamoylation of isoquinoline N-oxides with formylamides by means of dual C-H oxidative coupling

被引:31
作者
Yao, Bo [1 ]
Deng, Chen-Liang [1 ]
Liu, Yan [1 ]
Tang, Ri-Yuan [1 ]
Zhang, Xing-Guo [1 ]
Li, Jin-Heng [2 ]
机构
[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
[2] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Hunan, Peoples R China
基金
中国国家自然科学基金;
关键词
MONOXIDE-FREE AMINOCARBONYLATION; AMIDE BOND FORMATION; FACTOR XA INHIBITORS; ARYL HALIDES; DIRECT ARYLATION; CARBONYLATION REACTIONS; ATMOSPHERIC-PRESSURE; CARBON; AMIDATION; BROMIDES;
D O I
10.1039/c4cc10140e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new palladium-catalyzed oxidative carbamoylation reaction of isoquinoline N-oxides with formylamides for the synthesis of isoquinoline-1-carboxamides is established. The method represents the first example of the carbamoylation of isoquinoline N-oxides with formylamides to furnish arylamides using the dual C-H oxidation strategy.
引用
收藏
页码:4097 / 4100
页数:4
相关论文
共 75 条
[21]   Palladium-Catalyzed Oxidative Cross-Coupling between Pyridine N-Oxides and Indoles [J].
Gong, Xue ;
Song, Guoyong ;
Zhang, Hong ;
Li, Xingwei .
ORGANIC LETTERS, 2011, 13 (07) :1766-1769
[22]   Direct synthesis of amides from alcohols and amines with liberation of H2 [J].
Gunanathan, Chidambaram ;
Ben-David, Yehoshoa ;
Milstein, David .
SCIENCE, 2007, 317 (5839) :790-792
[23]   Synthesis and assay of isoquinoline derivatives as HIV-1 Tat-TAR interaction inhibitors [J].
He, MZ ;
Yuan, DK ;
Lin, W ;
Pang, RF ;
Yu, XL ;
Yang, M .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (17) :3978-3981
[24]   Direct amidation of azoles with formamides via metal-free C-H activation in the presence of tert-butyl perbenzoate [J].
He, Tao ;
Li, Hongji ;
Li, Pinhua ;
Wang, Lei .
CHEMICAL COMMUNICATIONS, 2011, 47 (31) :8946-8948
[25]  
Henry P.M., 1980, Palladium Catalyzed Oxidation of Hydrocarbons, V2
[26]   Expedient Synthesis of N-Acyl Anthranilamides and β-Enamine Amides by the Rh(III)-Catalyzed Amidation of Aryl and Vinyl C-H Bonds with Isocyanates [J].
Hesp, Kevin D. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (30) :11430-11433
[27]   Carbon monoxide free aminocarbonylation of aryl and alkenyl iodides using DMF as an amide source [J].
Hosoi, K ;
Nozaki, K ;
Hiyama, T .
ORGANIC LETTERS, 2002, 4 (17) :2849-2851
[28]   Chemical synthesis of natural product peptides: Coupling methods for the incorporation of noncoded amino acids into peptides [J].
Humphrey, JM ;
Chamberlin, AR .
CHEMICAL REVIEWS, 1997, 97 (06) :2243-2266
[29]   The Scope and Limitation of Nickel-Catalyzed Aminocarbonylation of Aryl Bromides from Formamide Derivatives [J].
Jo, Youngshin ;
Ju, Jinhun ;
Choe, Jaehoon ;
Song, Kwang Ho ;
Lee, Sunwoo .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) :6358-6361
[30]   Aminocarbonylation of aryl halides using a nickel phosphite catalytic system [J].
Ju, Jinhun ;
Jeong, Miso ;
Moon, Jeongju ;
Jung, Hyun Min ;
Lee, Sunwoo .
ORGANIC LETTERS, 2007, 9 (22) :4615-4618