Microwave-assisted preparation of fused bicyclic heteroaryl boronates: Application in one-pot Suzuki couplings

被引:28
作者
DiMauro, EF [1 ]
Vitullo, JR [1 ]
机构
[1] Amgen Inc, Dept Chem Res & Discovery, Cambridge, MA 02139 USA
关键词
D O I
10.1021/jo060218p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The rapid and efficient synthesis of various disubstituted 5,6-fused heterocycles using a microwave-assisted one-pot cyclization-Suzuki coupling approach is described. This work highlights the tolerance of the boronic ester functional group to a variety of reaction conditions and the utility of functionalized boronates as penultimate intermediates in the synthesis of diverse compound libraries.
引用
收藏
页码:3959 / 3962
页数:4
相关论文
共 31 条
[1]   Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].
Bellina, F ;
Carpita, A ;
Rossi, R .
SYNTHESIS-STUTTGART, 2004, (15) :2419-2440
[2]  
Besson T, 2007, MICROWAVE ASSISTED ORGANIC SYNTHESIS, P44
[3]   Total synthesis of an atropdiastereomer of RP-66453 and determination of its absolute configuration [J].
Bois-Choussy, M ;
Cristau, P ;
Zhu, JP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) :4238-4241
[4]  
Bridges A J, 1993, Bioorg Med Chem, V1, P403, DOI 10.1016/S0968-0896(00)82150-1
[5]   FLUORINE AS AN ORTHODIRECTING GROUP IN AROMATIC METALATION - A 2-STEP PREPARATION OF SUBSTITUTED BENZO[B]THIOPHENE-2-CARBOXYLATES [J].
BRIDGES, AJ ;
LEE, A ;
MADUAKOR, EC ;
SCHWARTZ, CE .
TETRAHEDRON LETTERS, 1992, 33 (49) :7499-7502
[6]  
D'Sa BA, 2001, SYNLETT, P670
[7]  
Dell C. P., 2000, SCI SYNTHESIS HOUBEN, V10, P11
[8]   Universal solid-phase approach for the immobilization, derivatization, and resin-to-resin transfer reactions of boronic acids [J].
Gravel, M ;
Thompson, KA ;
Zak, M ;
Bérubé, C ;
Hall, DG .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :3-15
[9]  
HAJOS G, 2002, SCI SYNTH, V12, P613
[10]   Synthesis of para-substituted 3-formyl arylboronic esters [J].
Holland, R ;
Spencer, J ;
Deadman, JJ .
SYNTHESIS-STUTTGART, 2002, (16) :2379-2382