Pyrido[1,2-c][1,2,4]triazol-3-ylidene: reactivity and its application in organocatalysis and organometallic catalysis.
The reactivity and catalytic performance of 2-ethylpyrido[1,2-c][1,2,4]-triazol-3-ylidene 6 have been comprehensively investigated. The carbene 6 has shown unusual properties owing to the effect of the pyrido-annulation. While formohydrazide 8 and hydrazine 9 are obtained via the destruction of the triazole skeleton of the carbene, 3-((1Z,3E)-4-(1H-pyrrol-1-yl)buta-1,3-dienyl)-1-ethyl-1H-1,2,4-triazole 10 is achieved through the cleavage of the C-N bond of the pyridine ring. The carbene has turned out to be a powerful catalyst in a variety of organocatalyzed and Pd(II)-catalyzed transformations.
Wei
Siping
S
Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064, People's Republic of China.
Liu
Bo
B
Zhao
Dongbing
D
Wang
Zhen
Z
Wu
Jie
J
Lan
Jingbo
J
You
Jingsong
J
D000171:Acrolein / Q000031:analogs & derivatives / Q000737:chemistry; D001965:Bromides / Q000737:chemistry; D002384:Catalysis; D009589:Nitrogen Oxides / Q000737:chemistry; D009603:Nitroso Compounds / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
D001965:Bromides; D009589:Nitrogen Oxides; D009603:Nitroso Compounds; D009942:Organometallic Compounds; D011725:Pyridines; D014230:Triazoles; C015388:nitrones; D010165:Palladium; D000171:Acrolein; C012843:cinnamaldehyde; C012456:nitrosobenzene