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Azavinyl azomethine ylides from thermal ring opening of alpha-aziridinohydrazones: unprecedented 1,5-electrocyclization to imidazoles.
- Source :
-
Organic letters [Org Lett] 2007 Aug 16; Vol. 9 (17), pp. 3461-4. Date of Electronic Publication: 2007 Jul 28. - Publication Year :
- 2007
-
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.
Details
- Language :
- English
- ISSN :
- 1523-7060
- Volume :
- 9
- Issue :
- 17
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 17661476
- Full Text :
- https://doi.org/10.1021/ol701522t