One pot synthesis of α-ketoamides from ethylarenes and amines: a metal free difunctionalization strategy

被引:17
作者
Ramanathan, Mani [1 ]
Kuo, Chun-Kai [1 ]
Liu, Shiuh-Tzung [1 ]
机构
[1] Natl Taiwan Univ, Dept Chem, Taipei 106, Taiwan
关键词
OXIDATIVE AMIDATION; ROOM-TEMPERATURE; METHYL KETONES; INHIBITORS; ACETOPHENONES; CATALYST; CARBONYLATION; AMINATION; ALKYNES; IODINE;
D O I
10.1039/c6ob02361d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
One-pot and metal free synthesis of alpha-ketoamides has been described through in situ generation of aryl ketones from easily available ethylarenes followed by amidation with various amines. This multiple oxidation protocol involves catalytic I-2-pyridine-TBHP (t-butyl hydroperoxide) mediated oxidative benzylic carbonylation and sequential NaI-TBHP mediated oxidative amidation without using any solvent.
引用
收藏
页码:11446 / 11453
页数:8
相关论文
共 48 条
[1]   Retinoid receptor subtype-selective modulators through synthetic modifications of RARγ agonists [J].
Alvarez, Susana ;
Alvarez, Rosana ;
Khanwalkar, Harshal ;
Germain, Pierre ;
Lemaire, Geraldine ;
Rodriguez-Barrios, Fatima ;
Gronemeyer, Hinrich ;
de Lera, Angel R. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (13) :4345-4359
[2]   The introduction of P4 substituted 1-methylcyclohexyl groups into Boceprevir®: A change in direction in the search for a second generation HCV NS3 protease inhibitor [J].
Bennett, Frank ;
Huang, Yuhua ;
Hendrata, Siska ;
Lovey, Raymond ;
Bogen, Stephane L. ;
Pan, Weidong ;
Guo, Zhuyan ;
Prongay, Andrew ;
Chen, Kevin X. ;
Arasappan, Ashok ;
Venkatraman, Srikanth ;
Velazquez, Francisco ;
Nair, Latha ;
Sannigrahi, Mousumi ;
Tong, Xiao ;
Pichardo, John ;
Cheng, Kuo-Chi ;
Girijavallabhan, Viyyoor M. ;
Saksena, Anil K. ;
Njoroge, F. George .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (08) :2617-2621
[3]   Effective oxidation of benzylic and alkane C-H bonds catalyzed by sodium o-iodobenzenesulfonate with Oxone as a terminal oxidant under phase-transfer conditions [J].
Cui, Li-Qian ;
Liu, Kai ;
Zhang, Chi .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (07) :2258-2265
[4]   Recent Developments in General Methodologies for the Synthesis of α-Ketoamides [J].
De Risi, Carmela ;
Pollini, Gian Piero ;
Zanirato, Vinicio .
CHEMICAL REVIEWS, 2016, 116 (05) :3241-3305
[5]   Iodine-Promoted Oxidative Amidation of Terminal Alkenes - Synthesis of α-Ketoamides, Benzothiazoles, and Quinazolines [J].
Deshidi, Ramesh ;
Devari, Shekaraiah ;
Shah, Bhahwal Ali .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (07) :1428-1432
[6]   A general metal free approach to α-ketoamides via oxidative amidation-diketonization of terminal alkynes [J].
Deshidi, Ramesh ;
Kumar, Manjeet ;
Devari, Shekaraiah ;
Shah, Bhahwal Ali .
CHEMICAL COMMUNICATIONS, 2014, 50 (67) :9533-9535
[7]   The syntheses of α-ketoamides via nBu4NI-catalyzed multiple sp3C-H bond oxidation of ethylarenes and sequential coupling with dialkylformamides [J].
Du, Bingnan ;
Jin, Bo ;
Sun, Peipei .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (26) :4586-4589
[8]   Didemnidines A and B, Indole Spermidine Alkaloids from the New Zealand Ascidian Didemnum sp. [J].
Finlayson, Rhys ;
Pearce, A. Norrie ;
Page, Michael J. ;
Kaiser, Marcel ;
Bourguet-Kondracki, Marie-Lise ;
Harper, Jacquie L. ;
Webb, Victoria L. ;
Copp, Brent R. .
JOURNAL OF NATURAL PRODUCTS, 2011, 74 (04) :888-892
[9]   A Metal-Free Amination of Benzoxazoles - The First Example of an Iodide-Catalyzed Oxidative Amination of Heteroarenes [J].
Froehr, Tanja ;
Sindlinger, Christian P. ;
Kloeckner, Ulrich ;
Finkbeiner, Peter ;
Nachtsheim, Boris J. .
ORGANIC LETTERS, 2011, 13 (14) :3754-3757
[10]   I2-Catalyzed C-O Bond Formation and Dehydrogenation: Facile Synthesis of Oxazolines and Oxazoles Controlled by Bases [J].
Gao, Wen-Chao ;
Hu, Fei ;
Huo, Yu-Ming ;
Chang, Hong-Hong ;
Li, Xing ;
Wei, Wen-Long .
ORGANIC LETTERS, 2015, 17 (15) :3914-3917