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Isoxazolines from Nitro Compounds: Synthesis and Applications

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Synthesis of Heterocycles via Cycloadditions I

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 12))

Abstract

This paper reviews the construction of isoxazoline rings via 1,3-dipolar cycloaddition of nitrile oxides or nitronates, including silyl nitronates, generated from nitroalkanes, with alkenes. Recent studies on the mechanism and regiochemistry, inter- and intramolecular versions and asymmetric approaches to the cycloaddition are also dealt with in this review. A comparison of the nitrile oxide cycloaddition with silyl nitronate cycloaddition, especially their intramolecular versions, indicates the superiority of the silyl nitronate approach in providing the cycloadducts in greater yield and selectivity. Finally, various modes of cleavage of the isoxazoline ring to potentially useful synthetic intermediates are also discussed.

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  1. Department of Chemistry, Indian Institute of Technology, 400 076, Bombay, Mumbai, India

    Irishi N. N. Namboothiri & Namrata Rastogi

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  1. Irishi N. N. Namboothiri
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  2. Namrata Rastogi
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Correspondence to Irishi N. N. Namboothiri .

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Alfred Hassner

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Namboothiri, I.N.N., Rastogi, N. (2008). Isoxazolines from Nitro Compounds: Synthesis and Applications. In: Hassner, A. (eds) Synthesis of Heterocycles via Cycloadditions I. Topics in Heterocyclic Chemistry, vol 12. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2007_101

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