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Bibas H, Moloney DW, Neumann R, et al. Chemistry of stable iminopropadienones, RN=C=C=C=O. J Org Chem. 2002;67(8):2619-31doi: 10.1021/jo0110552.
Bibas, H., Moloney, D. W., Neumann, R., Shtaiwi, M., Bernhardt, P. V., & Wentrup, C. (2002). Chemistry of stable iminopropadienones, RN=C=C=C=O. The Journal of organic chemistry, 67(8), 2619-31. https://doi.org/10.1021/jo0110552
Bibas, Hervé, et al. "Chemistry of stable iminopropadienones, RN=C=C=C=O." The Journal of organic chemistry vol. 67,8 (2002): 2619-31. doi: https://doi.org/10.1021/jo0110552
Bibas H, Moloney DW, Neumann R, Shtaiwi M, Bernhardt PV, Wentrup C. Chemistry of stable iminopropadienones, RN=C=C=C=O. J Org Chem. 2002 Apr 19;67(8):2619-31. doi: 10.1021/jo0110552. PMID: 11950308.
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J Org Chem. 2002 Apr 19;67(8):2619-31. doi: 10.1021/jo0110552.

Chemistry of stable iminopropadienones, RN=C=C=C=O.

The Journal of organic chemistry

Hervé Bibas, Daniel W J Moloney, Ralf Neumann, Majed Shtaiwi, Paul V Bernhardt, Curt Wentrup

Affiliations

  1. Chemistry Department, The University of Queensland, Brisbane, Queensland 4072, Australia.

PMID: 11950308 DOI: 10.1021/jo0110552

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).

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