Synthesis of novel fluorescent 3-aryl- and 3-methyl-7-aryl-[1,2,3]triazolo[1,5-a]pyridines by Suzuki cross-coupling reactions

被引:27
作者
Abarca, Belen
Aucejo, Ricardo
Ballesteros, Rafael
Blanco, Fernando
Garcia-Espana, Enrique
机构
[1] Fac Farm, Dept Quim Organ, Burjassot 46100, Valencia, Spain
[2] Inst Ciencia Mol ICMOL, Dept Quim Inorgan, Fac Quim, Burjassot 46100, Valencia, Spain
关键词
triazolopyridines; Suzuki cross-coupling reaction; fluorescence;
D O I
10.1016/j.tetlet.2006.09.051
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two series of compounds, 3-aryl-(series A, compounds 2a-j) and 3-methyl-7-aryl-[1,2,3]triazolo[1,5-a]pyridines (series B, compounds 3a-j) have been synthesized by Suzuki cross-coupling reactions, with a triazolopyridine halide and an aryl or heteroaryl boronic acid in moderate to good yields. All compounds obtained are fluorescents, the quantum yields, particularly those of compounds 3f-f, are very high. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8101 / 8103
页数:3
相关论文
共 15 条
[1]   Triazolopyridines. Part 24: New polynitrogenated potential helicating ligands [J].
Abarca, B ;
Ballesteros, R ;
Chadlaoui, M .
TETRAHEDRON, 2004, 60 (27) :5785-5792
[2]   Synthesis of novel triazolopyridylboronic acids and esters.: Study of potential application to Suzuki-type reactions [J].
Abarca, B ;
Ballesteros, R ;
Blanco, F ;
Bouillon, A ;
Collot, V ;
Domínguez, JR ;
Lancelot, JC ;
Rault, S .
TETRAHEDRON, 2004, 60 (22) :4887-4893
[3]   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
[4]   A facile route to new potential helicating ligands [J].
Abarca, B ;
Ballesteros, R ;
Elmasnaouy, M .
TETRAHEDRON, 1998, 54 (50) :15287-15292
[5]  
BOCCHI V, 1982, SYNTHESIS-STUTTGART, P1096
[6]   THE IDENTIFICATION OF C12H8N4O, AN OXIDATION PRODUCT FROM ALPHA-PYRIDIL MONOHYDRAZONE [J].
BOYER, JH ;
GOEBEL, N .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (02) :304-305
[7]  
Catrall R.W., 1997, CHEM SENSORS
[8]  
CHADLAOUI M, IN PRESS J ORG CHEM
[9]   Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].
Hassan, J ;
Sévignon, M ;
Gozzi, C ;
Schulz, E ;
Lemaire, M .
CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469
[10]   The chemistry of the triazolopyridines: an update [J].
Jones, G .
ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 83, 2002, 83 :1-70