Isomeric Isoxazolopyridinones: Synthesis, Tautomerism and Molecular Orbital Calculation.

Robert Weis; Klaus Schweiger; Walter Fabian

doi:10.3390/ecsoc-3-01723

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Isomeric Isoxazolopyridinones: Synthesis, Tautomerism and Molecular Orbital Calculation.

Robert Weis

^{*

1},

Klaus Schweiger

^{*

1},

Walter M. F. Fabian

^{*

2}

¹ Institute of Pharmaceutical Chemistry, Schubertstr. 1, Karl-Franzens University Graz, A-8010 Graz, Austria
² Institute of Organic Chemistry, Heinrichstr. 28 Karl-Franzens University Graz, A-8010 Graz, Austria

Published: 01 November 1999 by MDPI in The 3rd International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-3-01723

Abstract: Depending on the substituent at C-4 (OH or MeNH) 3-acyl-5,6-dihydropyridinones 1 and 2 react with hydroxylamine to give either isoxazolo[5,4-c]pyridinone 3 and isoxazolo[4,3-c]pyridinone 4, respectively. The tautomeric equilibria of 1 and 2 are investigated by means of NMR spectroscopy and density functional calculations. The mechanisms of formation of 3 and 4 are interpreted with the aid of semiempirical molecular orbital calculations.

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