Multicomponent cascade reactions: sequential [1 + 4] and [2 + 3] cycloadditions for the generation of heterocyclic ring systems.
[reaction: see text]. A novel intermolecular nitrile oxide cycloaddition sequence has been developed for the formation of highly substituted heterocyclic rings. Reaction of trimethylsilyl cyanide with epoxides generates isonitriles which can react with nitroalkenes to form N-(isoxazolylidene)alkylamines. After fragmentation to nitrile oxides, the dipoles can undergo intermolecular 1,3-dipolar cycloadditions with electron deficient dipolarophiles to generate substituted isoxazolines in one synthetic operation.
Fédou
Nicolas M
NM
Department of Chemistry, School of Life Sciences, University of Sussex, Falmer, Brighton, UK.
Parsons
Philip J
PJ
Viseux
Eddy M E
EM
Whittle
Alan J
AJ