Noble synthesis of the [1,4]-oxazine derivatives and its mechanistic study
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The [1,4]-oxazine structure is one of important backbone in natural products and biological activity compounds. However, there are fewer synthetic methods are reported. Herein, we are introducing of noble and convenient synthetic method of [1,4]-oxazine and their derivatives using 3-halo-4-hydroxy-prop-3-en-2-one / dihalo-hydroxy-but- 3-en-2-one and N-substituted-2-hydroxy / halo acetamide compound as starting materials. In addition, this method can be adaptable to synthesis of pyridazine, pyridine and naphthoquinone fused [1,4]- oxazines. Also, we are suggested that this reaction mechanism is followed via Michael type addition or SN2 type reaction between 3-halo-4-hydroxy-prop-3-en-2-one/dihalo-hydroxy-but-3-en-2-one and N- substituted-2-hydroxy / halo acetamide compound and then inter- molecular nitrogen oriented migration.