Sulfonamide-directed gold-catalyzed [2+2+2]-cycloadditions of nitriles with two discrete ynamides to construct 2,4-diaminopyridine cores

被引:55
作者
Chen, Yu-Ling [1 ]
Sharma, Pankaj [1 ]
Liu, Rai-Shung [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, 101,Sec 2,Kuang Fu Rd, Hsinchu 30043, Taiwan
关键词
2+2+2 CYCLOADDITIONS; ENANTIOSELECTIVE SYNTHESIS; RING-SYSTEMS; ALKYNES; DERIVATIVES; INHIBITORS; PYRIDINES; CYCLOTRIMERIZATION; DIYNES; ALPHA; OMEGA-DIYNES;
D O I
10.1039/c5cc09688j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Gold-catalyzed [2+2+2]-cycloadditions of two discrete ynamides and one nitrile afford 2,4-diaminopyridine derivatives that are not readily prepared from typical low-valent-metal catalysts. Our mechanistic analysis reveals that the reaction chemoselectivity is controlled by the types of sulfonamides of ynamides.
引用
收藏
页码:3187 / 3190
页数:4
相关论文
共 64 条
[1]   New ring systems from 1,2-benzisothiazole-1,1-dioxides and related compounds [J].
Abramovitch, RA ;
Shinkai, I ;
Mavunkel, BJ ;
More, KM ;
OConnor, S ;
Ooi, GH ;
Pennington, WT ;
Srinivasan, PC ;
Stowers, JR .
TETRAHEDRON, 1996, 52 (09) :3339-3354
[2]   Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2) [J].
Anderson, DR ;
Hegde, S ;
Reinhard, E ;
Gomez, L ;
Vernier, WF ;
Lee, L ;
Liu, S ;
Sambandam, A ;
Snider, PA ;
Masih, L .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (06) :1587-1590
[3]   Gold-catalyzed intermolecular Hetero-Dehydro-Diels-Alder cycloaddition of captodative dienynes with nitriles:: A new reaction and regioselective direct access to pyridines [J].
Barluenga, Jose ;
Fernandez-Rodriguez, Manuel Angel ;
Garcia-Garcia, Patricia ;
Aguilar, Enrique .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (09) :2764-+
[4]   Synthesis of macrocycles via cobalt-mediated [2+2+2] cycloadditions [J].
Boñaga, LVR ;
Zhang, HC ;
Moretto, AF ;
Ye, H ;
Gauthier, DA ;
Li, J ;
Leo, GC ;
Maryanoff, BE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) :3473-3485
[5]   [2+2+2] cycloaddition reactions catalyzed by transition metal complexes [J].
Chopade, Pramod R. ;
Louie, Janis .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2307-2327
[6]   Iron-Catalyzed Cycloaddition of Alkynenitriles and Alkynes [J].
D'Souza, Brendan R. ;
Lane, Timothy K. ;
Louie, Janis .
ORGANIC LETTERS, 2011, 13 (11) :2936-2939
[7]   An Investigation of Wall Effects in Microwave-Assisted Ring-Closing Metathesis and Cyclotrimerization Reactions [J].
Dallinger, Doris ;
Irfan, Muhammed ;
Suljanovic, Amra ;
Kappe, C. Oliver .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15) :5278-5288
[8]   Gold-Catalyzed Intermolecular [4+2] and [2+2+2] Cycloadditions of Ynamides with Alkenes [J].
Dateer, Ramesh B. ;
Shaibu, Balagopal S. ;
Liu, Rai-Shung .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (01) :113-117
[9]   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
[10]   ELECTRONIC AND STERIC EFFECTS IN THE RHODIUM-COMPLEX CATALYZED CO-CYCLIZATION OF ALKYNES AND NITRILES TO PYRIDINE-DERIVATIVES [J].
DIVERSI, P ;
ERMINI, L ;
INGROSSO, G ;
LUCHERINI, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 447 (02) :291-298