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Fluoroazoles. II. Synthesis and 1 H and 19 F Nmr spectra of 2‐, 4‐, and 5‐Fluoro‐1‐methylimidazole
Author(s) -
Fabra F.,
Gálvez C.,
González A.,
Viladoms P.,
Vilarrasa J.
Publication year - 1978
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570150731
Subject(s) - chemistry , tautomer , imidazole , nmr spectra database , ring (chemistry) , spectral line , medicinal chemistry , proton nmr , stereochemistry , organic chemistry , physics , astronomy
The three possible ring‐monofluorinated N ‐methylimidazoles have been prepared by photochemical irradiation of the corresponding diazonium tetrafluoroborates. 5‐Fluoro‐1‐methyl‐imidazole was also obtained by methylation of 1‐acetyl‐4‐fluoroimidazole. The 1 H and 19 F nmr spectra of these N ‐methylated fluoroazoles are compared, and the predominance of one tautomeric form in 4(5)‐fluoroimidazole is discussed.