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

Alberto Brandi; Franca M. Cordero; Francesco De Sarlo; Andrea Goti; Antonio Guarna

doi:10.1055/s-1993-22329

Synlett 1993; 1993(1): 1-8
DOI: 10.1055/s-1993-22329

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

Alberto Brandi^* , Franca M. Cordero, Francesco De Sarlo, Andrea Goti, Antonio Guarna

^*Dipartimento di Chimica organica "U. Schiff", Università di Firenze, I-50121 Firenze, Italy

Abstract

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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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