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Review

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

by and *,†
CSIRO Manufacturing, Bag 10, Clayton South MDC, Victoria 3169, Australia
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Mark A. Rizzacasa
Molecules 2016, 21(8), 935; https://doi.org/10.3390/molecules21080935
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)
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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MDPI and ACS Style

Meyer, A.G.; Ryan, J.H. 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives. Molecules 2016, 21, 935. https://doi.org/10.3390/molecules21080935

AMA Style

Meyer AG, Ryan JH. 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives. Molecules. 2016; 21(8):935. https://doi.org/10.3390/molecules21080935

Chicago/Turabian Style

Meyer, Adam G., and John H. Ryan 2016. "1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives" Molecules 21, no. 8: 935. https://doi.org/10.3390/molecules21080935

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