Acid-Catalyzed Pyridylimidazoline Rearrangement
G. E. SALNIKOV, I. A. KIRILYUK, D. A. MOROZOV, S. A. CHERKASOV, A. M. GENAEV
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russia
Keywords: 1-alkoxy-3-imidazolines, nitroxide radicals, imidazo[1,5-а]пиридин, rearrangement, superacids, NMR
Pages: 625-639
Abstract
1-Alkoxy-3-imidazolines derived from stable nitroxide radicals, as well as nitroxide radicals themselves, bearing the 2-pyridyl substituent in position 2, under mild conditions undergo acid-catalyzed rearrangement with the fragmentation of the imidazoline ring and the formation of imidazo[1,5-a]pyridine. This rearrangement does not occur in superacid media due to the protective protonation of the nitrogen atom of the pyridyl substituent.
|
