Microwave-Induced Molecular Rearrangements. Flash Thermolysis in the Gas-Phase and in Solution: Synthesis of Quinolones and Naphthyridones

Delphine Lecoq; Benjamin A. Chalmers; Rakesh N. Veedu; David Kvaskoff; Paul V. Bernhardt; Curt Wentrup

doi:10.1071/CH09447

RESEARCH ARTICLE

Microwave-Induced Molecular Rearrangements. Flash Thermolysis in the Gas-Phase and in Solution: Synthesis of Quinolones and Naphthyridones

Delphine Lecoq ^A , Benjamin A. Chalmers ^A , Rakesh N. Veedu ^A , David Kvaskoff ^A , Paul V. Bernhardt ^A and Curt Wentrup ^A ^B

+ Author Affiliations

- Author Affiliations

^A School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia.

^B Corresponding author. Email: wentrup@uq.edu.au

Australian Journal of Chemistry 62(12) 1631-1638 https://doi.org/10.1071/CH09447
Submitted: 26 August 2009 Accepted: 3 October 2009 Published: 10 December 2009

Abstract

3- and 4-Pyridyliminopropadienones were prepared by flash vacuum thermolysis of Meldrum’s acid derivatives and characterized by low temperature IR spectroscopy. They react with dimethylamine to afford 1,5-, 1,6-, and 1,7-naphthyridones. The same naphthyridones are also obtained by microwave irradiation of the Meldrum’s acid derivatives. Quinolones were obtained by microwave irradiation of phenylaminomethylene-Meldrum’s acids and 1-phenylpyrrole-2,3-diones.

Acknowledgements

This work was supported by the Australian Research Council. The authors thank the Centre for Computational Molecular Science at The University of Queensland for generous access to its supercomputer. D.L. thanks the Ecole Nationale Superieure d’Ingenieurs de Caen, France, for a travelling stipend.

References

Microwave-Induced Molecular Rearrangements. Flash Thermolysis in the Gas-Phase and in Solution: Synthesis of Quinolones and Naphthyridones

Abstract

Acknowledgements

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