Events The 3rd International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 3rd International Electronic Conference on Synthetic Organic Chemistry

Published date

01 Nov, 1999

Citation

Robert Weis, Klaus Schweiger, Walter M. F. Fabian, Isomeric Isoxazolopyridinones: Synthesis, Tautomerism and Molecular Orbital Calculation., in Proceedings of The 3rd International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 1999, MDPI: Basel, Switzerland, 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

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.

Keywords

n/a

Synthesis of 4,5-dihydroimidazole-2-carboxamides.

The T1 Linker: Multidirectional Cleavage for Solid Phase Organic Synthesis.