G. Hoornaert
Sep 1, 2010
Citations
0
Influential Citations
5
Citations
Journal
Bulletin des Sociétés Chimiques Belges
Abstract
The synthesis and functionalization of 3,5 dichloro-2(1H)pyrazinones and the corresponding 2H-1,4-oxazin-2-ones is described. The use of their multifunctionalized 2-azadiene system in cycloaddition reactions with electron-rich and electron-poor dienophiles and subsequent eliminations from the adducts of alkynes or nitriles is discussed. In this way pyridine or pyrazine derivatives can be obtained. Application of an intramolecular version of the cycloaddition-elimination process is shown to yield c-anellated 2(1H)pyridin(on)es from 2(1H)pyrazinones anchored with an appropriate side chain in position 3 or 6. The specific combination of a 2-azadiene system, 3-chlorimine group and a reactive lactone function in the 2H-1,4-oxazin-2-ones is demonstrated to generate specifically substituted oxazoles, triazoles and tetrazoles on reaction and further conversion with specific nucleophiles. The mechanism of these processes is briefly mentioned together with their application in the synthesis of nucleoside or alkaloid-type compounds.