New Synthesis of Azaheterocycles by Rearrangement of Isoxazoline-5-spirocycloalkane Compounds

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Abstract
The thermal rearrangement of 5-spiro(cyclopropane or cyclobutane)isoxazolines and isoxazolidines has established a new methodology for the synthesis of selectively functionalised azaheterocycles. The application of the two-step process to the synthesis of heterocycles of different size is presented. The process is particularly convenient for the synthesis of N-bridgehead heterocycles, and its application to the synthesis of natural products bearing this skeleton is described. 1. Introduction 2. The Rearrangement 3. Monocyclic Products: Pyridine and Azepine Derivatives 4. N-Bridgehead Heterocycles 4.1. The Nitrile Oxide Route: Sequential Rearrangement-Annulation of Isoxazoline-5-spirocyclopropanes 4.2. The Nitrone Route: Use of Endocyclic Nitrones 5. Conclusion

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