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Multicomponent cascade reactions: Sequential [1+4] and [2+3] cycloadditions for the generation of heterocyclic ring systems
journal contribution
posted on 2023-06-08, 07:51 authored by Nicolas M Fedou, Philip J Parsons, Eddy Viseux, Alan J WhittleA 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.
History
Publication status
- Published
Journal
Organic LettersISSN
1523-7060Publisher
American Chemical SocietyExternal DOI
Issue
15Volume
7Page range
3179-3182Pages
4.0Department affiliated with
- Chemistry Publications
Notes
EMEV did much of the early synthetic work and co wrote the paper under the direction of PJP This paper features a novel four-component cascade reaction for a number of examples. It describes a novel use of salt effects and microwave radiation to accelerate the rate of the cascade.Full text available
- No
Peer reviewed?
- Yes
Legacy Posted Date
2012-02-06Usage metrics
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