Fluoroquinolones from imidoylketenes and iminopropadienones, R-N=C=C=C=O

Fulloon, Belinda E. and Wentrup, Curt (2009) Fluoroquinolones from imidoylketenes and iminopropadienones, R-N=C=C=C=O. Australian Journal of Chemistry, 62 2: 115-120. doi:10.1071/CH08515

Author Fulloon, Belinda E.
Wentrup, Curt
Title Fluoroquinolones from imidoylketenes and iminopropadienones, R-N=C=C=C=O
Journal name Australian Journal of Chemistry   Check publisher's open access policy
ISSN 0004-9425: 448-0038
Publication date 2009-02-19
Sub-type Article (original research)
DOI 10.1071/CH08515
Volume 62
Issue 2
Start page 115
End page 120
Total pages 6
Editor Curt Wentrup
Place of publication Australia
Publisher CSIRO Publishing
Collection year 2010
Language eng
Subject C1
030503 Organic Chemical Synthesis
970103 Expanding Knowledge in the Chemical Sciences
Abstract 3-Fluoro-, 4-fluoro-, and 2,3,4-trifluorophenyliminopropadienones have been generated by flash vacuum thermolysis (FVT) of 5-[(fluoroarylamino)methoxymethylene]-2,2-dimethyldioxan-4,6-dione (Meldrum’s acid) derivatives. Their reaction with methanol affords interconverting imidoylketenes and oxoketenimines, which are employed in a synthesis of fluoroquinolones. The same quinolones are obtained from methyl 1-fluoroaryl-1,2,3-triazole-4-carboxylates, which on FVT eliminate N2 to generate oxoketenimines. Rearrangement of the oxoketenimines to imidoylketenes and cyclization afford the quinolones.
Q-Index Code C1
Q-Index Status Confirmed Code

Document type: Journal Article
Sub-type: Article (original research)
Collections: 2010 Higher Education Research Data Collection
School of Chemistry and Molecular Biosciences
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Citation counts: TR Web of Science Citation Count  Cited 13 times in Thomson Reuters Web of Science Article | Citations
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Created: Thu, 03 Sep 2009, 08:42:37 EST by Mr Andrew Martlew on behalf of School of Chemistry & Molecular Biosciences