title: 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives.
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.
authors.affiliation: CSIRO Manufacturing, Bag 10, Clayton South MDC, Victoria 3169, Australia. adam.meyer@csiro.au.
authors.forename: Adam G
authors.initials: AG
authors.lastname: Meyer
authors.affiliation: CSIRO Manufacturing, Bag 10, Clayton South MDC, Victoria 3169, Australia. jack.ryan@csiro.au.
authors.forename: John H
authors.initials: JH
authors.lastname: Ryan
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D010080:Oxazoles; D013882:Thiosemicarbazones; C512188:azomethine
keywords: aldehyde; anhydride; azomethine; carbonyl; cycloaddition; dipolar; ketone; oxazolidine; spiro; ylide