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
来源：
ARKIVOC | 2007年
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
  • [41] TRIAZOLOPYRIDINES .3. ATTEMPTS TO INTRODUCE SUBSTITUENTS INTO THE 6-MEMBERED RING OF 1,2,3-TRIAZOLO[1,5-A]PYRIDINE
    ABARCA, B
    HAYLES, DJ
    JONES, G
    SLISKOVIC, DR
    JOURNAL OF CHEMICAL RESEARCH-S, 1983, (06): : 144 - 144
  • [42] Combining Amines and 3-(2-Pyridyl)-[1,2,3]Triazolo[1,5-a]pyridine: An Easy Access to New Functional Polynitrogenated Ligands
    Chiassai, Leonardo
    Ballesteros-Garrido, Rafael
    Paz Clares, Maria
    Garcia-Espana, Enrique
    Ballesteros, Rafael
    Abarca, Belen
    SYNTHESIS-STUTTGART, 2019, 51 (21): : 4034 - 4042
  • [43] Triazolopyridines .19. Synthesis and reactions of ylides derived from [1,2,3]triazolo[1,5-a]quinoline and [1,2,3]triazolo[5,1-a]isoquinoline with methyl propiolate.
    Abarca, B
    Ballesteros, R
    Houari, N
    TETRAHEDRON, 1997, 53 (37) : 12765 - 12770
  • [44] Synthesis of novel fluorescent 3-aryl- and 3-methyl-7-aryl-[1,2,3]triazolo[1,5-a]pyridines by Suzuki cross-coupling reactions
    Abarca, Belen
    Aucejo, Ricardo
    Ballesteros, Rafael
    Blanco, Fernando
    Garcia-Espana, Enrique
    TETRAHEDRON LETTERS, 2006, 47 (46) : 8101 - 8103
  • [45] TRIAZOLOPYRIDINES .14. SUBSTITUTION-REACTIONS OF 7-AMINO[1,2,3]TRIAZOLO[1,5-A]PYRIDINES
    ASENSIO, A
    ABARCA, B
    JONES, G
    HURSTHOUSE, MB
    MALIK, KMA
    TETRAHEDRON, 1993, 49 (03) : 703 - 712
  • [46] Synthesis of 1,2,3-triazolo[1,5-a]pyridin-8-ium-3-olates
    Khazhieva, Inna S.
    Demkin, Pavel M.
    Nein, Julia I.
    Glukhareva, Tatiana V.
    Morzherin, Yuri Yu.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2015, 51 (02) : 199 - 202
  • [47] A new modular and flexible approach to [1,2,3]triazolo[1,5-a][1,4]benzodiazepines
    Alajarin, Mateo
    Cabrera, Jose
    Pastor, Aurelia
    Villalgordo, Jose M.
    TETRAHEDRON LETTERS, 2007, 48 (20) : 3495 - 3499
  • [48] Spectroscopic studies of the interaction of 3-(2-thienyl)-[1,2,3]triazolo[1,5-a]pyridine with 2,6-dimethyl-β-cyclodextrin and ctDNA
    Cifuentes, T.
    Cayupi, J.
    Celis-Barros, C.
    Zapata-Torres, G.
    Ballesteros, Rafael
    Ballesteros-Garrido, Rafael
    Abarca, B.
    Jullian, C.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (41) : 9760 - 9767
  • [49] Synthesis and tautomerization of 6,7-dihydro-(1,2,3)-triazolo[1,5-a]pyrimidines
    Desenko, Sergey M.
    Gladkov, Evgeny S.
    Shishkina, Svetlana V.
    Shishkin, Oleg V.
    Komykhov, Sergey A.
    Orlov, Valery D.
    Meier, Herbert
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (06) : 1563 - 1567
  • [50] An expedient and facile route for the general synthesis of 3-aryl substituted 1,2,3-triazolo[1,5-a][1,4]benzodiazepin-6-ones and 1,2,3-triazolo[1,5-a][1,5] benzodiazocin-7-ones
    Chowdhury, Chinmay
    Sasmal, Anup Kumar
    Achari, Basudeb
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (21) : 4971 - 4977
12345