Michael-type addition of aziridinecarboxylates to 1,2-diaza-1,3-butadienes resulted in the formation of α-aziridinohydrazone adducts. Upon refluxing in toluene, formation of imidazoles in moderate to good yields was observed. Such a reactivity pattern is well explained by 1,5-electrocyclization of azavinyl azomethine ylide generated through thermal ring opening of α-aziridinohydrazones.
Azavinyl azomethine ylides freom thermal ring opening af alfa-aziridinohydrazones: unprecedented 1,5-electrocyclization to imidazoles / O. A., Attanasi; Davoli, Paolo; G., Favi; P., Filippone; Forni, Arrigo; G., Moscatelli; Prati, Fabio. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - 9:17(2007), pp. 3461-3464. [10.1021/ol701522t]
Azavinyl azomethine ylides freom thermal ring opening af alfa-aziridinohydrazones: unprecedented 1,5-electrocyclization to imidazoles
DAVOLI, Paolo;FORNI, Arrigo;PRATI, Fabio
2007
Abstract
Michael-type addition of aziridinecarboxylates to 1,2-diaza-1,3-butadienes resulted in the formation of α-aziridinohydrazone adducts. Upon refluxing in toluene, formation of imidazoles in moderate to good yields was observed. Such a reactivity pattern is well explained by 1,5-electrocyclization of azavinyl azomethine ylide generated through thermal ring opening of α-aziridinohydrazones.
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