Premium
One‐step synthesis of N ‐[(methylthio)methyl]imidazole and related heterocyclic derivatives via a fummerer rearrangement
Author(s) -
Janzen A. F.,
Lypka G. N.,
Wasylishen R. E.
Publication year - 1979
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.5570160249
Subject(s) - chemistry , imidazole , benzimidazole , pyrazole , trimethylsilyl , medicinal chemistry , mass spectrometry , mass spectrum , combinatorial chemistry , organic chemistry , chromatography
N ‐[(Methylthio)methyl]imidazole may be prepared from dimethylsulfoxide and N ‐(trimethylsilyl)imidazole or N ‐( t ‐butyldimethylsilyl)imidazole at elevated temperatures via a Purnmerer rearrangement. The product was characterized by elemental analysis, mass spectrometry and proton and carbon nmr. Preliminary experiments show that corresponding derivatives of 2‐methylimidazole, pyrazole, triazole and benzimidazole may also be prepared in an analogous manner.