Azavinyl azomethine ylides from thermal ring opening of alpha-aziridinohydrazones: unprecedented 1,5-electrocyclization to imidazoles.
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.
Istituto di Chimica Organica, Università degli Studi di Urbino Carlo Bo, Via I Maggetti 24, 61029 Urbino, Italy. attanasi@uniurb.it
Orazio A
OA
Attanasi
Paolo
P
Davoli
Gianfranco
G
Favi
Paolino
P
Filippone
Arrigo
A
Forni
Giada
G
Moscatelli
Fabio
F
Prati