title: 1,3-Dipolar cycloaddition-decarboxylation reactions of an azomethine ylide with isatoic anhydrides: formation of novel benzodiazepinones.
abstract: A nonstabilized azomethine ylide reacts with a wide range of substituted isatoic anhydrides to afford novel 1,3-benzodiazepin-5-one derivatives, which are generally isolated in high yield. The transformations involve 1,3-dipolar cycloaddition reactions of the ylide with the anhydrides to give transient, and in a representative case spectroscopically observable, oxazolidine intermediates that undergo ring-opening-decarboxylation-ring-closing reaction cascades to yield the 1,3-benzodiazepin-5-one products.
authors.affiliation: CSIRO, Division of Materials Science and Engineering, Bag 10, Clayton South, Victoria 3169, Australia.
authors.forename: Asha M
authors.initials: AM
authors.lastname: D'Souza
authors.forename: Nadia
authors.initials: N
authors.lastname: Spiccia
authors.forename: Jose
authors.initials: J
authors.lastname: Basutto
authors.forename: Pawel
authors.initials: P
authors.lastname: Jokisz
authors.forename: Leon S-M
authors.initials: LS
authors.lastname: Wong
authors.forename: Adam G
authors.initials: AG
authors.lastname: Meyer
authors.forename: Andrew B
authors.initials: AB
authors.lastname: Holmes
authors.forename: Jonathan M
authors.initials: JM
authors.lastname: White
authors.forename: John H
authors.initials: JH
authors.lastname: Ryan
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D001570:Benzodiazepinones / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D010078:Oxazines / Q000737:chemistry*; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D001570:Benzodiazepinones; D010078:Oxazines; D013882:Thiosemicarbazones; C512188:azomethine; C037902:isatoic anhydride