Efficient cleavage of the N-O bond of 3,6-dihydro-1,2-oxazines mediated by some alpha-hetero substituted carbonyl compounds in mild conditions.
The efficient cleavage of the N-O bond of some nitroso Diels-Alder cycloadducts has been achieved in mild conditions, mediated either by 2,2-dimethyl-1,3-dioxan-5-one or 1,3-dithiolane-2-carboxaldehyde. These new and purely organic conditions allow an excellent tolerance with respect to many functional groups that would have been affected by previous reductive cleavage conditions.
Galvani
Gilles
G
Laboratoire de Procédés et Substances Naturelles, ICMMO-UMR 8182, Bâtiment 410-Université Paris-Sud XI, 15 rue Georges Clémenceau, 91405 Orsay Cedex, France.
Calvet
Géraldine
G
Blanchard
Nicolas
N
Kouklovsky
Cyrille
C
D000447:Aldehydes / Q000737:chemistry*; D004146:Dioxanes / Q000737:chemistry*; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D010078:Oxazines / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*
C529746:1,3-dithiolane-2-carboxaldehyde; C519900:2,2-dimethyl-1,3-dioxan-5-one; D000447:Aldehydes; D004146:Dioxanes; D006573:Heterocyclic Compounds, 1-Ring; D010078:Oxazines; D009584:Nitrogen; D010100:Oxygen