Room Temperature, Copper-Catalyzed Amination of Bromonaphthyridines with Aqueous Ammonia

被引:28
作者
Anderson, Cyrus A. [1 ]
Taylor, Phillip G. [1 ]
Zeller, Mary A. [1 ]
Zimmerman, Steven C. [1 ]
机构
[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA
关键词
HYDROGEN-BONDED HETERODIMERS; ARYL HALIDES; MOLECULAR RECOGNITION; C-N; HETEROCYCLIC UREAS; POLYMERS; COMPLEXATION; EFFICIENT; MECHANISMS; SULFONATES;
D O I
10.1021/jo100476x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Room temperature, copper-catalyzed amination of amido-bromo-1,8-naphthyridines is reported. Use of Cu2O and aqueous ammonia at ambient temperature affords amination products in 10-87% yield. Bromonaphthyridines are prepared in 15-65% yield via treatment of amidonaphthyridinones with phosphorus tribromide. This methodology provides an alternative route to functional, nonsymmetric 2,7-diamido-1,8-naphthyridines.
引用
收藏
页码:4848 / 4851
页数:4
相关论文
共 67 条
[31]  
Lüning U, 2002, EUR J ORG CHEM, V2002, P4063
[32]   Heterodimers for molecular recognition by fourfold hydrogen bonds [J].
Lüning, U ;
Kühl, C .
TETRAHEDRON LETTERS, 1998, 39 (32) :5735-5738
[33]   Atom transfer radical polymerization [J].
Matyjaszewski, K ;
Xia, JH .
CHEMICAL REVIEWS, 2001, 101 (09) :2921-2990
[34]   Synthesis of a soluble ureido-naphthyridine oligomer that self-associates via eight contiguous hydrogen bonds [J].
Mayer, MF ;
Nakashima, S ;
Zimmerman, SC .
ORGANIC LETTERS, 2005, 7 (14) :3005-3008
[35]   Cu-catalyzed azide-alkyne cycloaddition [J].
Meldal, Morten ;
Tornoe, Christian Wenzel .
CHEMICAL REVIEWS, 2008, 108 (08) :2952-3015
[36]   Catalytic C-C, C-N, and C-O Ullmann-Type Coupling Reactions [J].
Monnier, Florian ;
Taillefer, Marc .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (38) :6954-6971
[37]  
NEWKOME GR, 1981, J ORG CHEM, V46, P833, DOI 10.1021/jo00318a001
[38]   Higher affinity quadruply hydrogen-bonded complexation with 7-deazaguanine urea [J].
Ong, HC ;
Zimmerman, SC .
ORGANIC LETTERS, 2006, 8 (08) :1589-1592
[39]   A quadruply hydrogen bonded heterocomplex displaying high-fidelity recognition [J].
Park, T ;
Todd, EM ;
Nakashima, S ;
Zimmerman, SC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18133-18142
[40]   Preparation of 2,7-diamino-1,8-naphthyridine: A useful building block for supramolecular chemistry [J].
Park, T ;
Mayer, MF ;
Nakashima, S ;
Zimmerman, SC .
SYNLETT, 2005, (09) :1435-1436