A new efficient synthesis of pyrazoles from hydrazonoyl halides and β-oxophosphonates

[Display omitted] •1,3,5-Trisubstituted pyrazoles were synthesized efficiently with excellent regioselectivity.•Reaction was carried out at mild condition: room temperature.•Reaction was tolerated for many substrates with a wide scope of functional groups.•Reaction was carried out in good yield: the...

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Bibliographic Details
Published in:Tetrahedron letters 2014-01, Vol.55 (4), p.889-892
Main Authors: Sun, Aixue, Ye, Jia-Hai, Yu, Haitao, Zhang, Wenchao, Wang, Xiaolong
Format: Article
Language:English
Subjects:
Compatibility
Functional groups
Halides
Heterocycles
Hydrazonoyl halides
Phosphonates
Pyrazole
Pyrazoles
Regioselectivity
Synthesis (chemistry)
Tetrahedrons
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Summary:[Display omitted] •1,3,5-Trisubstituted pyrazoles were synthesized efficiently with excellent regioselectivity.•Reaction was carried out at mild condition: room temperature.•Reaction was tolerated for many substrates with a wide scope of functional groups.•Reaction was carried out in good yield: the yields of most products were higher than 80%.•A plausible reaction mechanism was proposed. A new practical and efficient synthesis of 1,3,5-trisubstituted pyrazoles has been developed by reacting of hydrazonoyl halides with β-oxophosphonates under mild conditions in good yields with excellent regioselectivity. This process employs an addition–elimination sequence. Wide scope, functional group compatibility has been established.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.12.045