Phospha-Michael additions of a series of methylene-bridged phosphorus bidentate nucleophiles to 1,2-diaza-1,3-dienes gave monoadducts and bisadducts in high yields under mild conditions. In particular, a series of new ylides and symmetrical diylides have been obtained from bis(diphenyl)phosphanes. The use of diphenylphosphanylamino derivatives gave, through phospha-Michael addition, ylide intermediates that underwent spontaneous intramolecular attack by the amino group belonging to the Michael donor reagent moiety, thus giving access to new heterocycles.
C. Boga, N. Zanna, O. A. Attanasi, G. Baccolini, L. De Crescentini, L. Forlani, et al. (2011). Phospha-Michael-Type Reactions between 1,2-Diaza-1,3-dienes and Bidentate Nucleophiles: Formation of New Mono- and Diylides and their Elaboration to Heterocycles. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, -(7), 1326-1334 [10.1002/ejoc.201001453].
Phospha-Michael-Type Reactions between 1,2-Diaza-1,3-dienes and Bidentate Nucleophiles: Formation of New Mono- and Diylides and their Elaboration to Heterocycles
BOGA, CARLA;ZANNA, NICOLA;BACCOLINI, GRAZIANO;FORLANI, LUCIANO;MICHELETTI, GABRIELE;TOZZI, SILVIA
2011
Abstract
Phospha-Michael additions of a series of methylene-bridged phosphorus bidentate nucleophiles to 1,2-diaza-1,3-dienes gave monoadducts and bisadducts in high yields under mild conditions. In particular, a series of new ylides and symmetrical diylides have been obtained from bis(diphenyl)phosphanes. The use of diphenylphosphanylamino derivatives gave, through phospha-Michael addition, ylide intermediates that underwent spontaneous intramolecular attack by the amino group belonging to the Michael donor reagent moiety, thus giving access to new heterocycles.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.