Cyclization of 4-Azido-3-nitroquinolines to Oxadiazolo[3,4-c]quinolines

Corinna Gressl; A. Elisabeth Täubl; Werner Fiala; Wolfgang Stadlbauer

doi:10.3390/ecsoc-14-00487

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Cyclization of 4-Azido-3-nitroquinolines to Oxadiazolo[3,4-c]quinolines

Corinna Gressl

A. Elisabeth Täubl

Werner Fiala

Wolfgang Stadlbauer

¹ Institut für Chemie, Organic Synthesis Group, Karl-Franzens-University of Graz, Heinrichstrasse 28, A-8010 Graz (Austria)

Published: 02 November 2010 by MDPI in The 14th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-14-00487

Abstract: 3-Nitro-4-chloroquinoline 3 was converted to the azides 5/6. The azides were cyclized on thermolysis to furoxanes 7/8. Deoxygenation to furazane 9 was achieved by reaction with triphenylphosphane. The reaction conditions were studied by differential scanning calorimetry (DSC). The azides 5/6 gave with triphenylphosphane the phosphazenes 10/11, which were cleaved to the aminoquinolone 12

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Corinna Gressl

A. Elisabeth Täubl

Werner Fiala

Wolfgang Stadlbauer