1435914-41-2Relevant academic research and scientific papers
One-pot synthesis of N-(imidazo[1,2-a]pyridin-3-yl)-and N-(imidazo[2,1-b][1,3]thiazol-5-yl)sulfonamides
Rozentsveig, Igor B.,Serykh, Valery Y.,Chernysheva, Gulnur N.,Chernyshev, Kirill A.,Kondrashov, Evgeniy V.,Tretyakov, Evgeny V.,Romanenko, Galina V.
, p. 368 - 375 (2013/02/25)
The reaction of 2-aminopyridines or 2-aminothiazole with N-(2,2-dichloro-2-phenylethylidene)arensulfonamides affords the corresponding products of nucleophilic addition to the azomethine group, N-[2,2-dichloro-2- phenyl-1-(heterylamino)ethyl]sulfonamides, in good yields. The latter are easily cyclized to (imidazo[1,2-a]pyridin-3-yl)sulfonamides and (imidazo[2,1-b] thiazol-5-yl)sulfonamides in the presence of alkali, whereas the expected isomeric (imidazo[1,2-a]pyridin-2-yl)sulfonamides and (imidazo[2,1-b]thiazol-6- yl)sulfonamides are not formed. A one-pot two-stage method for the synthesis of target heterocyclic compounds without the isolation of intermediates has been developed. A tentative mechanism of the formation of annulated heterocyclic derivatives has been proposed.
