The Synthesis of 3-Functionalized 5-chloro-6-methyl-2H-1,4-oxazin-2-ones and of pyridines from cycloaddition-elimination reactions with substituted acetylenic compounds.

Add time:07/26/2019    Source:sciencedirect.com

Selective functionalisation of the chlorimine group in 3,5-dichloro-6-methyl-2H-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-2H-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.

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