Secondary Amine Mediated Ring-Opening of Tetrahydroimidazo[1,5- b ][1,2,4]oxadiazol-2(1 H )-ones

Authors : Necdet COŞKUN

Pages : 267-272

View : 18 | Download : 10

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :5,6,7,7a-Tetrahydroimidazo [1,5- b ][1,2,4]oxadiazol-2insert ignore into journalissuearticles values(1 H );-ones 1a-g converted to imidazoles in the presence of secondary amines. cis-Imidazooxadiazolones 1d-g gave the imidazoles 4d-g when treated with secondary amines, while the treatment of these compounds with tertiary amines afforded imidazoline 3-oxides 5d-g. In case of 1a-c, where R1 is a hydrogen, tertiary amines induced elimination to give imidazoles 4a-c. In the case of 1a-c, probable trans elimination caused by triethylamine and pyridine and in the case of 1d-f, a concerted double cis elimination mediated by secondary amines is discussed.
Keywords : Turk J Chem, 25, 2001, 267 272 Turk J Chem, vol 25, iss 3