147591-73-9Relevant academic research and scientific papers
2-SUBSTITUTED IMIDAZOLES. 3. METALLATION OF 1-METHYL-2-PHENYL- AND 1-METHYL-2-(FURYL-2)IMIDAZOLES
Stoyanov, V. M.,El'chaninov, M. M.,Pozharskii, A. F.
, p. 53 - 57 (1992)
1-Methyl-2-phenylimidazole reacts with butyllithium to give 5-lithium substituted products.On the other hand, 1-methyl-2-(furyl-2)imidazole is metallated under the same conditions exclusively on the furan ring and primarily in the 3 position.The introduction of triethylamine into the reaction mixture, or replacement of butyllithium by lithium 2,2,6,6-tetramethylpiperidide leads to the formation of a lithium derivative substituted at the 5-position of the furan ring exclusively.
