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

0556553 - ÚOCHB 2023 RIV US eng J - Journal Article
Motornov, Vladimir - Beier, Petr
Access to Fluoroalkylated Azoles and 2-Acylaminoketones via Fluorinated Anhydride-Mediated Cleavage of NH-1,2,3-Triazoles.
Organic Letters. Roč. 24, č. 10 (2022), s. 1958-1963. ISSN 1523-7060. E-ISSN 1523-7052
R&D Projects: GA MŠMT LTAUSA18037
Institutional support: RVO:61388963
Keywords : inhibitors * heterocycles * amination
OECD category: Organic chemistry
Impact factor: 5.2, year: 2022
Method of publishing: Limited access
https://doi.org/10.1021/acs.orglett.2c00359

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-triazines was developed by a one-pot two-step route from NH-triazoles, fluorinated anhydrides, and amines or hydrazine.
Permanent Link: http://hdl.handle.net/11104/0330791