Selective C-N Bond-Forming Reaction of 2,6-Dibromopyridine with Amines

被引:33
作者
Wang, Lei [1 ]
Liu, Ning [1 ]
Dai, Bin [1 ]
Hu, Hengcai [1 ]
机构
[1] Shihezi Univ, Sch Chem & Chem Engn, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi 832003, Xinjiang, Peoples R China
关键词
Synthetic methods; Nitrogen heterocycles; Cross-coupling; Copper; Amines; COMPLEX CATALYSTS BEARING; TRANSFER HYDROGENATION; IRAK-4; INHIBITORS; COUPLING REACTIONS; ARYL HALIDES; LIGAND; AGGREGATION; ARYLATION; PYRAZOLES; SERIES;
D O I
10.1002/ejoc.201402619
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical and efficient protocol for the syntheses of 6-substituted 2-bromopyridine compounds has been developed by using a selective copper-catalyzed C-N bond-forming reaction between 2,6-dibromopyridine and a range of amines. The major advantage of this protocol is the complete control of selectivity of the pyridine bromine atom for the C-N cross-coupling reaction. There are few reported syntheses of unsymmetrical 2,6-disubstituted pyridine-bridged compounds because of their complicated preparations. Although this is the case, a new series of these unsymmetrical compounds have been successfully prepared in two steps by using this copper-catalyzed coupling approach.
引用
收藏
页码:6493 / 6500
页数:8
相关论文
共 45 条
[1]   The copper-catalyzed N-arylation of indoles [J].
Antilla, JC ;
Klapars, A ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11684-11688
[2]   Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles [J].
Antilla, JC ;
Baskin, JM ;
Barder, TE ;
Buchwald, SL .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5578-5587
[3]   Access to 2-Aminopyridines - Compounds of Great Biological and Chemical Significance [J].
Bolliger, Jeanne L. ;
Oberholzer, Miriam ;
Frech, Christian M. .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (06) :945-954
[4]   IRAK-4 inhibitors.: Part III:: A series of imidazo[1,2-a] pyridines [J].
Buckley, George M. ;
Fosbeary, Richard ;
Fraser, Joanne L. ;
Gowers, Lewis ;
Higueruelo, Alicia P. ;
James, Lynwen A. ;
Jenkins, Kerry ;
Mack, Stephen R. ;
Morgan, Trevor ;
Parry, David M. ;
Pitt, William R. ;
Rausch, Oliver ;
Richard, Marianna D. ;
Sabin, Verity .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (12) :3656-3660
[5]   IRAK-4 inhibitors.: Part II:: A structure-based assessment of imidazo[1,2-a]pyridine binding [J].
Buckley, George M. ;
Ceska, Thomas A. ;
Fraser, Joanne L. ;
Gowers, Lewis ;
Groom, Colin R. ;
Higueruelo, Alicia Perez ;
Jenkins, Kerry ;
Mack, Stephen R. ;
Morgan, Trevor ;
Parry, David M. ;
Pitt, William R. ;
Rausch, Oliver ;
Richard, Marianna D. ;
Sabin, Verity .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (11) :3291-3295
[6]   IRAK-4 inhibitors. Part 1: A series of amides [J].
Buckley, George M. ;
Gowers, Lewis ;
Higueruelo, Alicia Perez ;
Jenkins, Kerry ;
Mack, Stephen R. ;
Morgan, Trevor ;
Parry, David M. ;
Pitt, William R. ;
Rausch, Oliver ;
Richard, Marianna D. ;
Sabin, Verity ;
Fraser, Joanne L. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (11) :3211-3214
[7]   Structure-Property Relationships in Metallosupramolecular Poly(p-xylylene)s [J].
Burnworth, Mark ;
Rowan, Stuart J. ;
Weder, Christoph .
MACROMOLECULES, 2012, 45 (01) :126-132
[8]   1,1′-(pyridine-2,6-diyl)bis(3-benzyl-2,3-dihydro-1H-immidazol-2-ylidene), a new multidentate N-heterocyclic biscarbene and its silver(I) complex derivative [J].
Caballero, A ;
Díez-Barra, E ;
Jalón, FA ;
Merino, S ;
Tejeda, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) :395-398
[9]   Aqueous-phase, palladium-catalyzed cross-coupling of aryl bromides under mild conditions, using water-soluble, sterically demanding alkylphosphines [J].
DeVasher, RB ;
Moore, LR ;
Shaughnessy, KH .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :7919-7927
[10]   Copper(II) complex with tridentate N donor ligand: Synthesis, crystal structure, reactivity and DNA binding study [J].
Dey, Sourav ;
Sarkar, Sandipan ;
Paul, Hena ;
Zangrando, Ennio ;
Chattopadhyay, Pabitra .
POLYHEDRON, 2010, 29 (06) :1583-1587