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 50 条
  • [1] Fused mesoionic heterocycles:: synthesis of [1,2,3]triazolo[1,5-a]quinoline, [1,2,3]triazolo[1,5-a]quinazoline, [1,2,3]triazolo[1,5-a]quinoxaline and [1,2,3]triazolo[5,1-c]benzotriazine derivatives
    Abbott, PA
    Bonnert, RV
    Caffrey, MV
    Cage, PA
    Cooke, AJ
    Donald, DK
    Furber, M
    Hill, S
    Withnall, J
    TETRAHEDRON, 2002, 58 (16) : 3185 - 3198
  • [2] TRIAZOLOPYRIDINES .8. NUCLEOPHILIC-SUBSTITUTION REACTIONS OF 5-BROMO[1,2,3]TRIAZOLO[5,1-A]ISOQUINOLINE AND 7-BROMO[1,2,3]-TRIAZOLO[1,5-A]PYRIDINE
    ABARCA, B
    MOJARRED, F
    JONES, G
    PHILLIPS, C
    NG, N
    WASTLING, J
    TETRAHEDRON, 1988, 44 (10) : 3005 - 3014
  • [3] The chemistry of [1,2,3]triazolo[1,5-a ]pyridines
    Abarca-González, B
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2002, 17 (06) : 359 - 367
  • [4] Evaluation of the Novel Antichagasic Activity of [1,2,3]Triazolo[1,5-a]pyridine Derivatives
    Lapier, Michel
    Zuniga-Lopez, Maria C.
    Aguilera-Venegas, Benjamin
    Adam, Rosa
    Abarca, Belen
    Ballesteros, Rafael
    Lopez-Munoz, Rodrigo
    Diego Maya, Juan
    Olea-Azar, Claudio
    CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2017, 17 (04) : 399 - 411
  • [5] TRIAZOLOPYRIDINES .16. LITHIATION OF 3-CYANO[1,2,3]TRIAZOLO[1,5-A]-PYRIDINE
    JONES, G
    MOUAT, DJ
    PITMAN, MA
    LUNT, E
    LYTHGOE, DJ
    TETRAHEDRON, 1995, 51 (40) : 10969 - 10978
  • [6] [1,2,3]TRIAZOLO[1,5-A]PYRIDINE - A SYNTHON FOR 6-SUBSTITUTED PYRIDINE-2-CARBOXALDEHYDES
    JONES, G
    SLISKOVIC, DR
    TETRAHEDRON LETTERS, 1980, 21 (47) : 4529 - 4530
  • [7] THE REACTIONS OF 1,2,3-TRIAZOLO[1,5-A]PYRIDINE WITH ELECTROPHILES
    JONES, G
    SLISKOVIC, DR
    FOSTER, B
    ROGERS, J
    SMITH, AK
    WONG, MY
    YARHAM, AC
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (01): : 78 - 81
  • [8] A Convenient Synthesis of [1,2,3]Triazolo[1,5-a]quinoline
    Pokhodylo, N. T.
    Obushak, M. D.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 55 (08) : 1241 - 1243
  • [9] The Chemistry of the [1,2,3]Triazolo[1,5-a]pyridines: An Update
    Jones, Gurnos
    Abarca, Belen
    ADVANCES IN HETEROCYLIC CHEMISTRY, VOL 100, 2010, 100 : 195 - 252
  • [10] A Convenient Synthesis of [1,2,3]Triazolo[1,5-a]quinoline
    N. T. Pokhodylo
    M. D. Obushak
    Russian Journal of Organic Chemistry, 2019, 55 : 1241 - 1243