3-(2-Pyridyl)-[1,2,3]triazolo[1,5-a]pyridines.: An experimental and theoretical (DFT) study of the ring-chain isomerization

被引：50

作者：

Abarca, B

Alkorta, I

Ballesteros, R

Blanco, F

Chadlaoui, M

Elguero, J

Mojarrad, F

机构：

[1] Univ Valencia, Fac Farm, Dept Quim Organ, E-46100 Valencia, Spain

[2] CSIC, Inst Quim Med, E-28006 Madrid, Spain

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2005年 / 3卷 / 21期

关键词：

D O I：

10.1039/b510535h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An experimental (H-1 NMR) and theoretical (DFT) study of the ring-chain-ring isomerization of 3-(2-pyridyl)-[1,2,3]triazolo[1,5-a]pyrid-7-yl derivatives (A) into 6-{[1,2,3]triazolo[1,5-a]pyrid-3-yl}-2-pyridyl derivatives (B) has been carried out. Based on the calculations, a mechanism of several steps will be proposed. The experimental results as well as the calculations lead to the conclusion that the A-B ratio depends on the electronic properties of the substituents.

引用

收藏

页码：3905 / 3910

页数：6

相关论文

共 17 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 22.: Description of new 7,9-di(2-pyridyl)[1,2,3]triazolo[5′1′:6,1]pyrido[3,2-d]pyrimidines [J].

Abarca, B ;

Ballesteros, R ;

Chadlaoui, M .

ARKIVOC, 2002, :52-60

[4] 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

[5] A facile route to new potential helicating ligands [J].

Abarca, B ;

Ballesteros, R ;

Elmasnaouy, M .

TETRAHEDRON, 1998, 54 (50) :15287-15292

[6] Triazolopyridines 20. Hydrogenation reactions [J].

Abarca, B ;

Ballesteros, R ;

Elmasnouy, M .

TETRAHEDRON, 1999, 55 (44) :12881-12884

[7]

Bartolotti L.J., 1996, REV COMP CHEM, V7, P187, DOI [10.1002/9780470125847.ch4, DOI 10.1002/9780470125847.CH4]

[8] THE AZOMETHINE LINKAGE OF PYRIDINE IN RING-CLOSURE ISOMERIZATIONS [J].

BOYER, JH ;

BORGERS, R ;

WOLFORD, LT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (03) :678-680

[9]

Calero R, 2003, J CHIL CHEM SOC, V48, P85, DOI 10.4067/S0717-97072003000200015

[10]

EISTERT B, 1970, LIEBIGS ANN CHEM, V734, P56