R. Yurchenko, N. Svarovskaya, A. D. Ponomarenko
Jun 1, 2001
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Journal
Chemistry of Heterocyclic Compounds
Abstract
Imidazopyridines and many adamantane derivatives have appreciable physiologically active properties, an important role in which is played by the nature of the substituents in the molecule. 2-(Adamantan-1-yl)imidazo[1,2-a]pyridine (1a) was described earlier in [1], but no functional derivatives have been known up to now for it. In this report, we propose an improved method for obtaining compound 1a and present the results of a study of some of its chemical transformations. By heating 2-aminopyridine with bromomethyl (adamantan-1-yl) ketone in ethylacetate, followed by boiling the alkylation product 2 in acetic acid, we synthesized compound 1a in 84% yield (compare with [1]). We have established that compound 1a exhibits the chemical properties that are typical for imidazo[1,2-a]pyridines [2]: when treated with elemental bromine under conditions described in [2], the monobromo derivative 1b is formed, is nitrosated by sodium nitrite converting to compound 1c.