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.
9
17
3461
3464
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]
O. A., Attanasi; Davoli, Paolo; G., Favi; P., Filippone; Forni, Arrigo; G., Moscatelli; Prati, Fabio
File in questo prodotto:
File Dimensione Formato  
ol701522t azavinyl azomethin ylides to imidazoles (ASAP).pdf

non disponibili

Tipologia: Pre-print dell'autore (bozza pre referaggio)
Dimensione 76.38 kB
Formato Adobe PDF
76.38 kB Adobe PDF   Visualizza/Apri   Richiedi una copia
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

Licenza Creative Commons
I metadati presenti in IRIS UNIMORE sono rilasciati con licenza Creative Commons CC0 1.0 Universal, mentre i file delle pubblicazioni sono rilasciati con licenza Attribuzione 4.0 Internazionale (CC BY 4.0), salvo diversa indicazione.
In caso di violazione di copyright, contattare Supporto Iris

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11380/309480
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 34
  • ???jsp.display-item.citation.isi??? 33
social impact