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Molecules 2016, 21(8), 935; doi:10.3390/molecules21080935

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives

CSIRO Manufacturing, Bag 10, Clayton South MDC, Victoria 3169, Australia
These authors contributed equally to this work.
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Academic Editor: Mark A. Rizzacasa
Received: 31 May 2016 / Revised: 2 July 2016 / Accepted: 6 July 2016 / Published: 23 July 2016
(This article belongs to the Special Issue Pericyclic Reactions)

Abstract

We provide a comprehensive account of the 1,3-dipolar cycloaddition reactions of azomethine ylides with carbonyl dipolarophiles. Many different azomethine ylides have been studied, including stabilized and non-stabilized ylides. Of the carbonyl dipolarophiles, aldehydes including formaldehyde are the most studied, although there are now examples of cycloadditions with ketones, ketenes and carboxyl systems, in particular isatoic anhydrides and phthalic anhydrides. Intramolecular cycloadditions with esters can also occur under certain circumstances. The oxazolidine cycloadducts undergo a range of reactions triggered by the ring-opening of the oxazolidine ring system. View Full-Text
Keywords: dipolar; cycloaddition; azomethine; ylide; carbonyl; aldehyde; ketone; anhydride; oxazolidine; spiro dipolar; cycloaddition; azomethine; ylide; carbonyl; aldehyde; ketone; anhydride; oxazolidine; spiro
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Meyer, A.G.; Ryan, J.H. 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives. Molecules 2016, 21, 935.

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