First Efficient Palladium-Catalyzed Aminations of Pyrimidines, 1,2,4-Triazines and Tetrazines by Original Methyl Sulfur Release

被引:10
作者
Pellegatti, Laurent [1 ]
Vedrenne, Emeline [1 ]
Leger, Jean-Michel [2 ]
Jarry, Christian [2 ]
Routier, Sylvain [1 ]
机构
[1] Univ Orleans, Inst Chim Organ & Analyt, UMR CNRS 6005, F-45067 Orleans 2, France
[2] Univ Bordeaux 2, EA Pharmacochim 4138, F-33076 Bordeaux, France
关键词
aminations; cross-coupling; palladium; copper; sulfur; DIELS-ALDER REACTIONS; ARYL;
D O I
10.1055/s-0029-1217699
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The efficient and original palladium-catalyzed amination of pyrimidines, 1,2,4-triazines and tetrazines is reported. Starting from triazine 1, a Buchwald-Hartwig-type reaction leads to the formation of heterocycle 2 via methyl sulfur release. This reaction was generalized to the use of a wide range of amines in good to excellent yields.
引用
收藏
页码:2137 / 2142
页数:6
相关论文
共 32 条
[1]   A general approach to selective functionalization of 1,2,4-triazines using organometallics in palladium-catalyzed cross-coupling and addition reactions [J].
Alphonse, FA ;
Suzenet, F ;
Keromnes, A ;
Lebret, B ;
Guillaumet, G .
SYNTHESIS-STUTTGART, 2004, (17) :2893-2899
[2]   Copper(I)-promoted palladium-catalyzed cross-coupling of unsaturated tri-n-butylstannane with heteroaromatic thioether [J].
Alphonse, FA ;
Suzenet, F ;
Keromnes, A ;
Lebret, B ;
Guillaumet, G .
ORGANIC LETTERS, 2003, 5 (06) :803-805
[3]  
[Anonymous], ANGEW CHEM INT ED
[4]   New possibilities of 1,2,4-triazines functionalization: first examples of synthesis and structure of boron-containing 1,2,4-triazines [J].
Azev, Y ;
Lork, E ;
Duelcks, T ;
Gabel, D .
TETRAHEDRON LETTERS, 2004, 45 (16) :3249-3252
[5]   Intramolecular inverse electron demand Diels-Alder reactions of tryptamine with tethered heteroaromatic azadienes [J].
Benson, SC ;
Lee, L ;
Yang, L ;
Snyder, JK .
TETRAHEDRON, 2000, 56 (09) :1165-1180
[6]   Heteroaromatic thioether-organostannane cross-coupling [J].
Egi, M ;
Liebeskind, LS .
ORGANIC LETTERS, 2003, 5 (06) :801-802
[8]   Easy access to 3-or 5-heteroarylamino-1,2,4-triazines by SNAr, SNH, and palladium-catalyzed N-heteroarylations [J].
Garnier, E ;
Audoux, J ;
Pasquinet, E ;
Suzenet, F ;
Poullain, D ;
Lebret, B ;
Guillaumet, G .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :7809-7815
[10]   Practical asymmetric synthesis of a non-peptidic αvβ3 antagonist [J].
Keen, SP ;
Cowden, CJ ;
Bishop, BC ;
Brands, KMJ ;
Davies, AJ ;
Dolling, UH ;
Lieberman, DR ;
Stewart, GW .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (05) :1771-1779