Pyridylcarbene formation by thermal decomposition of 7-bromo-3-methyl-[1,2,3] triazolo[ 1,5-a] pyridine under pressure

被引:8
作者
Abarca, Belen [1 ]
Ballesteros, Rafael [1 ]
Blanco, Fernando [1 ]
机构
[1] Univ Valencia, Fac Farm, Dept Quim Organ, Avda Vicente Andres Estelles S-N, Valencia 46100, Spain
关键词
pyridylcarbene; high pressure reaction; triazolopyridines decomposition;
D O I
10.3998/ark.5550190.0008.426
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
7-Bromo-3-methyl-[1,2,3]triazolo[1,5- a] pyridine 1 at 1.7 atm and 100 degrees C decompose to form a pyridylcarbene intermediate by nitrogen expulsion. The carbene stabilization give 2-bromo-6-vinylpyridine 2, 1-(6-bromopyridin-2-yl) ethanol 3, 1-(6-Bromopyridin-2-yl) ethanone 4, 2bromo- 6-[ 2-( 6- bromopyridin- 2- yl)- 2- methyl- trans- cyclopropyl] pyridine 5, and 2- bromo- 6-[ 2-( 6bromopyridin-2-yl)-2-methyl-cis-cyclopropyl] pyridine 6.
引用
收藏
页码:297 / 303
页数:7
相关论文
共 18 条
[1]   3-(2-Pyridyl)-[1,2,3]triazolo[1,5-a]pyridines.: An experimental and theoretical (DFT) study of the ring-chain isomerization [J].
Abarca, B ;
Alkorta, I ;
Ballesteros, R ;
Blanco, F ;
Chadlaoui, M ;
Elguero, J ;
Mojarrad, F .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (21) :3905-3910
[2]  
ABARCA B, 1988, TETRAHEDRON, V44, P3005
[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]   NUCLEOPHILIC SUBSTITUTIONS ON BROMOTRIAZOLOPYRIDINES - AN IMPROVED ROUTE TO 2,6-DISUBSTITUTED PYRIDINES AND TO 1,3-DISUBSTITUTED ISOQUINOLINES [J].
ABARCA, B ;
BALLESTEROS, R ;
JONES, G ;
MOJARRAD, F .
TETRAHEDRON LETTERS, 1986, 27 (30) :3543-3546
[5]   Synthesis of novel fluorescent 3-aryl- and 3-methyl-7-aryl-[1,2,3]triazolo[1,5-a]pyridines by Suzuki cross-coupling reactions [J].
Abarca, Belen ;
Aucejo, Ricardo ;
Ballesteros, Rafael ;
Blanco, Fernando ;
Garcia-Espana, Enrique .
TETRAHEDRON LETTERS, 2006, 47 (46) :8101-8103
[6]   The chemistry of [1,2,3]triazolo[1,5-a ]pyridines [J].
Abarca-González, B .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2002, 17 (06) :359-367
[7]   CoII chemistry of 2,6-bis(2-pyridylcarbonyl)pyridine:: An icosanuclear Co cluster exhibiting superparamagnetic relaxation [J].
Boudalis, AK ;
Raptopoulou, CP ;
Abarca, B ;
Ballesteros, R ;
Chadlaoui, M ;
Tachagues, JP ;
Terzis, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (03) :432-435
[8]   PREPARATION, PROPERTIES, AND REACTIONS OF CARBONYL OXIDES [J].
BUNNELLE, WH .
CHEMICAL REVIEWS, 1991, 91 (03) :335-362
[9]  
CHADLAOUI M, IN PRESS J ORG CHEM
[10]  
CHADLOUI M, 2005, THESIS U VALENCIA