Chemoselective alkynylation of N-sulfonylamides versus amides and carbamates - Synthesis of tetrahydropyrazines

被引:62
作者
Aubineau, Thomas [1 ]
Cossy, Janine [1 ]
机构
[1] CNRS, Lab Chim Organ Associe, F-75231 Paris 05, France
关键词
HETEROCYCLES;
D O I
10.1039/c3cc40529j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The chemoselective alkynylation of N-sulfonylamides versus amides and carbamates using TMS-EBX as an alkynylating agent leads to the formation of non-symmetrical tetrahydropyrazines from orthogonally protected diamines.
引用
收藏
页码:3303 / 3305
页数:3
相关论文
共 18 条
[1]   Electrophilic alkynylation: the dark side of acetylene chemistry [J].
Brand, Jonathan P. ;
Waser, Jerome .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (11) :4165-4179
[2]   Ethynyl Benziodoxolones for the Direct Alkynylation of Heterocycles: Structural Requirement, Improved Procedure for Pyrroles, and Insights into the Mechanism [J].
Brand, Jonathan P. ;
Chevalley, Clara ;
Scopelliti, Rosario ;
Waser, Jerome .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (18) :5655-5666
[3]   Synthesis of Ketene N,N-Acetals by Copper-Catalyzed Double-Amidation of 1,1-Dibromo-1-alkenes [J].
Coste, Alexis ;
Couty, Francois ;
Evano, Gwilherm .
ORGANIC LETTERS, 2009, 11 (19) :4454-4457
[4]   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
[5]   SYNTHESIS OF CHIRAL PIPERAZIN-2-ONES AS MODEL PEPTIDOMIMETICS [J].
DIMAIO, J ;
BELLEAU, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (09) :1687-1689
[6]   Syntheses and transformations of piperazinone rings. A review [J].
Dinsmore, CJ ;
Beshore, DC .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2002, 34 (04) :367-+
[7]   Irregularities in the Effect of Potassium Phosphate in Ynamide Synthesis [J].
Dooleweerdt, Karin ;
Birkedal, Henrik ;
Ruhland, Thomas ;
Skrydstrup, Troels .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (23) :9447-9450
[8]  
Evano G., 2013, SYNTHESIS-STUTTGART, P17
[9]   Ynamides: Versatile Tools in Organic Synthesis [J].
Evano, Gwilherm ;
Coste, Alexis ;
Jouvin, Kevin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (16) :2840-2859
[10]   Copper-catalyzed 1,2-double amination of 1-halo-1-alkynes. Concise synthesis of protected tetrahydropyrazines and related heterocyclic compounds [J].
Fukudome, Yasuhiro ;
Naito, Hiroyuki ;
Hata, Takeshi ;
Urabe, Hirokazu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (06) :1820-+