Access to Fluoroalkylated Azoles and 2-Acylaminoketones via Anhydride-Mediated Cleavage of NH-1,2,3-Triazoles

17 February 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


NH-1,2,3-Triazoles undergo a ring cleavage in reactions with fluorinated acid anhydrides (trifluoroacetic, difluoroacetic chlorodifluoroacetic and pentafluoropropionic anhydrides) by nitrogen acylation and acid-mediated triazole ring opening. Structurally diverse fluoroalkylated oxazoles were prepared from 4,5-disubstituted-1,2,3-triazoles. Efficient synthesis of 2-acylaminoketones was achieved from 4-substituted-1,2,3-triazoles. Finally, easy access to fluoroalkylated imidazoles and 1,2,4-tetrazines was developed by one-pot two step routes from fluorinated anhydrides and NH-triazoles.


nitrogen heterocycles
vinyl cation

Supplementary materials

Access to Fluoroalkylated Azoles and 2-Acylaminoketones via Anhydride- Mediated Cleavage of NH-1,2,3-Triazoles
Experimental methods and copies of NMR spectra (PDF)


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