Synthesis of novel triazolopyridylboronic acids and esters.: Study of potential application to Suzuki-type reactions

被引:31
作者
Abarca, B
Ballesteros, R
Blanco, F
Bouillon, A
Collot, V
Domínguez, JR
Lancelot, JC
Rault, S
机构
[1] Univ Valencia, Fac Farm, Dept Quim Organ, E-46100 Valencia, Spain
[2] Ctr Etudes & Rech Medicament Normandie, F-14032 Caen, France
关键词
triazolopyridines; triazoloisoquinolines; boronic acids and esters; Suzuki cross-coupling reaction;
D O I
10.1016/j.tet.2004.03.083
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This paper describes a general method for the synthesis of novel [1,2,3]triazolo[1,5-a]pyridylboronic acids and esters, and the first results on Suzuki cross-coupling reactions with these new compounds and [1,2,3]triazolo[5,1-a]isoquinolylboronic acid, reacting with a variety of aryl halides as a route to 7-aryltriazolopyridines and 5-aryltriazoloisoquinolines. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4887 / 4893
页数:7
相关论文
共 23 条
[1]   Triazolopyridines 23.: Synthesis of 5,5′-bi[1,2,3]triazolo[5,1-a]isoquinoline [J].
Abarca, B ;
Ballesteros, R ;
Gay, B ;
Domínguez, JR .
ARKIVOC, 2004, :42-47
[2]   TRIAZOLOPYRIDINES .7. PREPARATION OF BROMO-TRIAZOLOPYRIDINES AND BROMO-TRIAZOLOISOQUINOLINES [J].
ABARCA, B ;
BALLESTEROS, R ;
MOJARRED, F ;
JONES, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (08) :1865-1868
[3]   Mechanistic studies of the ring opening reactions of [1,2,3]triazolo[1,5-a]pyridines [J].
Abarca, B ;
Ballesteros, R ;
Rodrigo, G ;
Jones, G ;
Veciana, J ;
Vidal-Gancedo, J .
TETRAHEDRON, 1998, 54 (33) :9785-9790
[4]   A facile route to new potential helicating ligands [J].
Abarca, B ;
Ballesteros, R ;
Elmasnaouy, M .
TETRAHEDRON, 1998, 54 (50) :15287-15292
[5]  
Abarca B., 1990, J CHEM RES, V9, P347
[6]   SEQUENTIAL DIRECTED ORTHO METALATION BORONIC ACID CROSS-COUPLING REACTIONS - A GENERAL REGIOSPECIFIC ROUTE TO OXYGENATED DIBENZO[B,D]PYRAN-6-ONES RELATED TO ELLAGIC ACID [J].
ALO, BI ;
KANDIL, A ;
PATIL, PA ;
SHARP, MJ ;
SIDDIQUI, MA ;
SNIECKUS, V ;
JOSEPHY, PD .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3763-3768
[7]   Synthesis of novel halopyridinylboronic acids and esters. Part 4: Halopyridin-2-yl-boronic acids and esters are stable, crystalline partners for classical Suzuki cross-coupling [J].
Bouillon, A ;
Lancelot, JC ;
Santos, JSD ;
Collot, V ;
Bovy, PR ;
Rault, S .
TETRAHEDRON, 2003, 59 (50) :10043-10049
[8]   Synthesis of novel halopyridinylboronic acids and esters. Part 1: 6-Halopyridin-3-yl-boronic acids and esters [J].
Bouillon, A ;
Lancelot, JC ;
Collot, V ;
Bovy, PR ;
Rault, S .
TETRAHEDRON, 2002, 58 (14) :2885-2890
[9]  
BOWER DJ, 1957, J CHEM SOC, P4506
[10]   In situ formation and reaction of 2-pyridylboronic esters [J].
Fuller, AA ;
Hester, HR ;
Salo, EV ;
Stevens, EP .
TETRAHEDRON LETTERS, 2003, 44 (14) :2935-2938