Azavinyl azomethine ylides from thermal ring opening of alpha-aziridinohydrazones: unprecedented 1,5-electrocyclization to imidazoles

Org Lett. 2007 Aug 16;9(17):3461-4. doi: 10.1021/ol701522t. Epub 2007 Jul 28.

Abstract

Michael-type addition of aziridinecarboxylates to 1,2-diaza-1,3-butadienes under solvent-free conditions (SFC) resulted in the formation of alpha-aziridinohydrazone adducts. In toluene under reflux, alpha-aziridinohydrazones gave imidazoles in moderate to good yields. Such a reactivity pattern is explained by 1,5-electrocyclization of azavinyl azomethine ylide generated through thermal ring opening of alpha-aziridinohydrazones.