title: Chemistry of stable iminopropadienones, RN=C=C=C=O.
abstract: The synthesis, spectroscopic properties, and chemical reactions of the stable (neopentylimino)-, (mesitylimino)-, and (o-tert-butylphenylimino)propadienones (6) are reported. Nucleophilic addition of amines affords the malonic amidoamidines 7 and 8. 3,5-Dimethylpyrazole reacts analogously to form 9b. Addition of 1,2-dimethylhydrazine produces pyrazolinones 10-12. Addition of N,N'-dimethyldiaminoethane, -propane, and -butane gives diazepine, diazocine, and diazonine derivatives 13-15, respectively (X-ray structures of 13c, 14a, and 15a are available). The mesoionic pyridopyrimidinium olates 18 are obtained by addition of 2-(methylamino)pyridine (X-ray structure of 18b available). Primary 2-aminopyridines afford the pyridopyrimidininones 20-29 and 31 (X-ray structure of 21a available), and 2-aminopyrimidines and 2-aminopyrazine afford pyrimidopyrimidinones and pyrazinopyrimidinones 33-35. Pyrimidoisoquinolinone 36 results from 1-aminoisoquinoline and pyridoquinolinone 40 from 8-aminoquinoline. 2-Aminothiazoline and 2-aminothiazole afford thiazolopyrimidinone derivatives 41-43 (X-ray structure of 43a available).
authors.affiliation: Chemistry Department, The University of Queensland, Brisbane, Queensland 4072, Australia.
authors.forename: Hervé
authors.initials: H
authors.lastname: Bibas
authors.forename: Daniel W J
authors.initials: DW
authors.lastname: Moloney
authors.forename: Ralf
authors.initials: R
authors.lastname: Neumann
authors.forename: Majed
authors.initials: M
authors.lastname: Shtaiwi
authors.forename: Paul V
authors.initials: PV
authors.lastname: Bernhardt
authors.forename: Curt
authors.initials: C
authors.lastname: Wentrup