Aken Koen Jeanne Alfons Van, G. Lux, G. Deroover
Apr 25, 1994
Citations
0
Influential Citations
22
Citations
Journal
Tetrahedron
Abstract
Abstract Selective functionalisation of the chlorimine group in 3,5-dichloro-6-methyl-2 H -1,4-oxazin-2-one is usually realised in appropriate conditions, by electrophilic catalysis avoiding reaction of the lactone function. The azadiene system in the 3-substituted 5-chloro-6-methyl-2 H -1,4-oxazin-2-ones is shown to react easily with monosubstituted acetylenic compounds yielding polyfunctionalized pyridines in excellent yield via a cycloaddition-elimination process. The usually high regioselectivity and its dependence on the nature of the 3-substituent is discussed.