Synthesis and selected transformations of 2-unsubstituted 1-(adamantyloxy)imidazole 3-oxides: straightforward access to non-symmetric 1,3-dialkoxyimidazolium salts

• Grzegorz Mlostoń,
• Małgorzata Celeda,
• Katarzyna Urbaniak,
• Marcin Jasiński,
• Vladyslav Bakhonsky,
• Peter R. Schreiner and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2019, 15, 497–505, doi:10.3762/bjoc.15.43

• ; nucleophilic carbenes; sulfur transfer reaction; Introduction Imidazole N-oxides constitute a practically valuable class of five-membered aromatic N-heterocycles [1][2][3][4][5]. The subclass of 2-unsubstituted imidazole N-oxides 1 with diverse substituents located at N(1), C(4), and C(5) is of special

• . Deoxygenation of 1-(adamantyloxy)imidazole 3-oxides 7a–d and isomerization of 7b into imidazole-2-one 9. Conversions of imidazole 3-oxides 7a–d into 1-(adamantyloxy)imidazole-2-thiones 10a–d via sulfur transfer reaction. Syntheses of the non-symmetric 1,3-dialkoxyimidazolium bromides 13a–c and 1-alkyl-3