Copper-catalyzed direct oxidative synthesis of α-ketoamides from aryl methyl ketones, amines, and molecular oxygen

被引:156
作者
Du, Feng-Tian [1 ,2 ]
Ji, Jian-Xin [1 ]
机构
[1] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China
[2] Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
DOUBLE CARBONYLATION; CYCLOTHEONAMIDE-B; AMIDE INHIBITORS; SINGLET OXYGEN; CORE STRUCTURE; DERIVATIVES; CLEAVAGE; ENAMINES; COMPLEX; SUPEROXIDE;
D O I
10.1039/c1sc00312g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel and efficient copper-catalyzed direct oxidative synthesis of alpha-ketoamides from aryl methyl ketones, amines, and molecular oxygen has been developed under mild and neat conditions. O-18 labeling experiments revealed that both oxygen atoms of the alpha-ketoamides derived from molecular oxygen.
引用
收藏
页码:460 / 465
页数:6
相关论文
共 57 条
[1]   Synthesis of α-Keto-Imides via Oxidation of Ynamides [J].
Al-Rashid, Ziyad F. ;
Johnson, Whitney L. ;
Hsung, Richard P. ;
Wei, Yonggang ;
Yao, Pei-Yuan ;
Liu, Renhei ;
Zhao, Kang .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :8780-8784
[2]   Hydroxylation of an aliphatic C-H bond in an imidazole-ligated (mu-eta(2):eta(2)-peroxo)dicopper(II) complex [J].
Allen, WE ;
Sorrell, TN .
INORGANIC CHEMISTRY, 1997, 36 (08) :1732-1734
[3]   SINGLET OXYGEN REACTION .4. PHOTOOXYGENATION OF ENAMINES INVOLVING A 2-STEP CLEAVAGE OF 1,2-DIOXETANE INTERMEDIATE [J].
ANDO, W ;
SAIKI, T ;
MIGITA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (17) :5028-5029
[4]   STUDIES ON THE OXIDATION OF ENAMINES WITH MOLECULAR-OXYGEN .2. OXIDATION OF 1-AMINO BUT-1-ENES [J].
BLAU, K ;
KAPST, U ;
VOERCKEL, V .
JOURNAL FUR PRAKTISCHE CHEMIE, 1989, 331 (04) :671-676
[5]   Copper-mediated nuclease activity of a tambjamine alkaloid [J].
Borah, S ;
Melvin, MS ;
Lindquist, N ;
Manderville, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (19) :4557-4562
[6]   Zinc Chloride Promoted Formal Oxidative Coupling of Aromatic Aldehydes and Isocyanides to α-Ketoamides [J].
Bouma, Marinus ;
Masson, Geraldine ;
Zhu, Jieping .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (08) :2748-2751
[7]   P2-achiral, P'-extended α-ketoamide inhibitors of calpain I [J].
Chatterjee, S ;
Dunn, D ;
Tao, M ;
Wells, G ;
Gu, ZQ ;
Bihovsky, R ;
Ator, MA ;
Siman, R ;
Mallamo, JP .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (16) :2371-2374
[8]   Design, synthesis, and biological evaluation of isoquinoline-1,3,4-trione derivatives as potent caspase-3 inhibitors [J].
Chen, YH ;
Zhang, YH ;
Zhang, HJ ;
Liu, DZ ;
Gu, M ;
Li, JY ;
Wu, F ;
Zhu, XZ ;
Li, J ;
Nan, F .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (05) :1613-1623
[9]   Synthesis and study of a lipophilic α-keto amide inhibitor of pancreatic lipase [J].
Chiou, A ;
Markidis, T ;
Constantinou-Kokotou, V ;
Verger, R ;
Kokotos, G .
ORGANIC LETTERS, 2000, 2 (03) :347-350
[10]  
Christ T, 2001, ANGEW CHEM INT EDIT, V40, P4192, DOI 10.1002/1521-3773(20011119)40:22<4192::AID-ANIE4192>3.0.CO