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Issue 46, 2016
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Cascade oxime formation, cyclization to a nitrone, and intermolecular dipolar cycloaddition

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Abstract

Simple haloaldehydes, including enolisable aldehydes, were found to be suitable for the formation of cyclic products by cascade (domino) condensation, cyclisation, dipolar cycloaddition chemistry. This multi-component reaction approach to heterocyclic compounds was explored by using hydroxylamine, a selection of aldehydes, and a selection of activated dipolarophiles. Initial condensation gives intermediate oximes that undergo cyclisation with displacement of halide to give intermediate nitrones; these nitrones undergo in situ intermolecular dipolar cycloaddition reactions to give isoxazolidines. The cycloadducts from using dimethyl fumarate were treated with zinc/acetic acid to give lactam products and this provides an easy way to prepare pyrrolizinones, indolizinones, and pyrrolo[2,1-a]isoquinolinones. The chemistry is illustrated with a very short synthesis of the pyrrolizidine alkaloid macronecine and a formal synthesis of petasinecine.

Graphical abstract: Cascade oxime formation, cyclization to a nitrone, and intermolecular dipolar cycloaddition

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Publication details

The article was received on 25 Aug 2016, accepted on 30 Oct 2016 and first published on 01 Nov 2016


Article type: Paper
DOI: 10.1039/C6OB01871H
Citation: Org. Biomol. Chem., 2016,14, 10953-10962
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    Cascade oxime formation, cyclization to a nitrone, and intermolecular dipolar cycloaddition

    R. C. Furnival, R. Saruengkhanphasit, H. E. Holberry, J. R. Shewring, H. D. S. Guerrand, H. Adams and I. Coldham, Org. Biomol. Chem., 2016, 14, 10953
    DOI: 10.1039/C6OB01871H

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