Multicomponent cascade reactions: Sequential [1+4] and [2+3] cycloadditions for the generation of heterocyclic ring systems

Fedou, Nicolas M, Parsons, Philip J, Viseux, Eddy M E and Whittle, Alan J (2005) Multicomponent cascade reactions: Sequential [1+4] and [2+3] cycloadditions for the generation of heterocyclic ring systems. Organic Letters, 7 (15). pp. 3179-3182. ISSN 1523-7060

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Abstract

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.

Item Type: Article
Additional Information: 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.
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: Philip Parsons
Date Deposited: 06 Feb 2012 20:48
Last Modified: 14 May 2012 14:04
URI: http://sro.sussex.ac.uk/id/eprint/28192
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