A facile transformation of alkynes into α-amino ketones by an N-bromosuccinimide-mediated one-pot strategy

被引:6
作者
Wei, Ting [1 ]
Zeng, Yongming [1 ,2 ]
He, Wei [1 ]
Geng, Lili [1 ]
Hong, Liang [1 ]
机构
[1] Changji Univ, Dept Chem & Appl Chem, Changji 831100, Peoples R China
[2] Nanjing Univ, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China
关键词
alpha-Amino ketones; N-Bromosuccinimide; Alkynes; One-pot synthesis; HIGHLY EFFICIENT SYNTHESIS; C-H AMINATION; METHYLENEDIOXYPYROVALERONE MDPV; COMBINATION; ALCOHOLS; DOPAMINE; BASE; HYDROGENATION; TRANSPORTER; IMIDATION;
D O I
10.1016/j.cclet.2018.03.031
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A facile transformation of alkynes into alpha-amino ketones by an N-bromosuccinimide-mediated one-pot cascade strategy is described. A variety of alpha-amino ketones are obtained in moderate to good yields under mild conditions. To overcome the multi-step synthesis, N-bromosuccinimide is involved in multiple tasks, playing a key role in the reaction course. (C) 2018 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码:383 / 385
页数:3
相关论文
共 54 条
[1]   Expanding the Scope of Donor/Acceptor Carbenes to N-Phthalimido Donor Groups: Diastereoselective Synthesis of 1-Cyclopropane α-Amino Acids [J].
Alford, Joshua S. ;
Davies, Huw M. L. .
ORGANIC LETTERS, 2012, 14 (23) :6020-6023
[2]   Hybrid Dopamine Uptake Blocker-Serotonin Releaser Ligands: A New Twist on Transporter-Focused Therapeutics [J].
Blough, Bruce E. ;
Landavazo, Antonio ;
Partilla, John S. ;
Baumann, Michael H. ;
Decker, Ann M. ;
Page, Kevin M. ;
Rothman, Richard B. .
ACS MEDICINAL CHEMISTRY LETTERS, 2014, 5 (06) :623-627
[3]   Palladium-catalyzed synthesis of 2-amino ketones from propargylic carbonates and secondary amines [J].
Cacchi, Sandro ;
Fabrizi, Giancarlo ;
Filisti, Eleonora ;
Goggiamani, Antonella ;
Iazzetti, Antonia ;
Maurone, Loredana .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (24) :4699-4703
[4]   Catalytic Asymmetric Bromoamination of Chalcones: Highly Efficient Synthesis of Chiral α-Bromo-β-Amino Ketone Derivatives [J].
Cai, Yunfei ;
Liu, Xiaohua ;
Hui, Yonghai ;
Jiang, Jun ;
Wang, Wentao ;
Chen, Weiliang ;
Lin, Lili ;
Feng, Xiaoming .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (35) :6160-6164
[5]   Mephedrone and methylenedioxypyrovalerone (MDPV), major constituents of "bath salts," produce opposite effects at the human dopamine transporter [J].
Cameron, Krasnodara ;
Kolanos, Renata ;
Verkariya, Rakesh ;
De Felice, Louis ;
Glennon, Richard A. .
PSYCHOPHARMACOLOGY, 2013, 227 (03) :493-499
[6]   Synthesis and Biological Evaluation of Bupropion Analogues as Potential Pharmacotherapies for Cocaine Addiction [J].
Carroll, F. Ivy ;
Blough, Bruce E. ;
Abraham, Philip ;
Mills, Andrew C. ;
Holleman, J. Ashley ;
Wolckenhauer, Scott A. ;
Decker, Ann M. ;
Landavazo, Antonio ;
McElroy, K. Timothy ;
Navarro, Hernan A. ;
Gatch, Michael B. ;
Forster, Michael J. .
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (21) :6768-6781
[7]   AgF/TFA-promoted highly efficient synthesis of α-haloketones from haloalkynes [J].
Chen, Zheng-Wang ;
Ye, Dong-Nai ;
Ye, Min ;
Zhou, Zhong-Gao ;
Li, Shen-Huan ;
Liu, Liang-Xian .
TETRAHEDRON LETTERS, 2014, 55 (07) :1373-1375
[8]   Nonselective bromination-selective debromination strategy: Selective bromination of unsymmetrical ketones on singly activated carbon against doubly activated carbon [J].
Choi, HY ;
Chi, DY .
ORGANIC LETTERS, 2003, 5 (04) :411-414
[9]   A facile debromination reaction: Can bromide now be used as a protective group in aromatic systems? [J].
Choi, HY ;
Chi, DY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :9202-9203
[10]   Ynamides: A Modern Functional Group for the New Millennium [J].
DeKorver, Kyle A. ;
Li, Hongyan ;
Lohse, Andrew G. ;
Hayashi, Ryuji ;
Lu, Zhenjie ;
Zhang, Yu ;
Hsung, Richard P. .
CHEMICAL REVIEWS, 2010, 110 (09) :5064-5106