Construction of novel spiroisoxazolines via intramolecular cyclization/methylation |
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| Authors: | Erick D Ellis Edward J Valente |
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| Institution: | a Department of Chemistry and Biochemistry, College of Science, Engineering and Technology, Jackson State University, Jackson, MS 39217, USA
b Department of Chemistry, University of Portland, Portland, OR 97203, USA |
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| Abstract: | Improved yields for the syntheses of a variety of spiroisoxazolines were achieved through intramolecular cyclization/methylation reactions of functionalized 5,5-disubstituted isoxazolines in one reaction vessel. Aromatic ring containing nitrile oxides and disubstituted geminal alkenes reacted in a 1,3-dipolar fashion to afford the corresponding 5,5-isoxazoline. A comparison of the relative location of the nucleophile and electrophile on the isoxazoline and two different ester functional groups was performed in order to determine the best isoxazoline system for the intramolecular cyclization/methylation reaction. |
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| Keywords: | Intramolecular cyclization Cycloaddition Regioselectivity Spirocycles Heterocycles |
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