Kauffmann, Thomas; Nuernberg, Reinhard; Schulz, Jutta; Stabba, R. published the artcile< Hetarynes. X. Detection of a 5-membered ring aryne (1-methyl-4,5-dehydroimidazole)>, Application In Synthesis of 1003-21-0, the main research area is IMIDAZOLES ARYNE; DEHYDROIMIDAZOLES; ARYNE IMIDAZOLES.
Treating 5-chloro-1-methylimidazole (I) and 5-bromol-1-methylimidazole (II) with Li piperidide/piperidine (III) in boiling ether gave a mixture of 4-piperidino-1-methylimidazole (IV) and 5-piperidino-1-methylimidazole (V). Analogous results using Li pyrrolidide (VI)/pyrrolidine (VII) base pair suggested that IV and V were formed through an elimination-addition mechanism on the title compound (VIII). The mechanism was elucidated by competing reactions of I and II with varying ratios of VII-III base pairs which resulted in IV, V, 5-pyrrolidinyl-1-methylimidazole, and 4-pyrrolidinyl-1-methylimidazole (IX). Anal. of product distribution indicated that the rearranged substitution products IV and IX were prepared through the elimination-addition mechanism, whereas the non-rearranged substitution products resulted from an overlap of the elimination-addition and the normal addition-elimination mechanism, in each case confirming the presence of VIII. Study on competitive reaction of 3-chloropyridine and 4-chloropyridine with the base-pair diethylamine/diisopropylamine confirmed the conclusion that all reactions with II follow the elimination-addition mechanism over the poorly selective intermediate VIII. With chloro compounds such as I, the normal addition-elimination mechanism becomes more important.
Tetrahedron Letters published new progress about 1003-21-0. 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, Application In Synthesis of 1003-21-0.
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem