air, rt

Scheme 14 Synthesis of cyanodioxanes using acylacetonitrile building blocks

104]. Benzoylacetonitrile was oxidized with manganese(III) acetate in the presence of 1,1-diphenylethene at room temperature in air and gave 4-cyano-3,6,6-triphenyl-1,2-dioxan-3-ol in 86% yield (Scheme 14) [105]. This was a very simple and convenient reaction for forming substituted 1,2-dioxanes without any by-products and with only simple temperature monitoring in air as a stipulation. Accordingly, the reaction was applied to many alkenes and acylacetonitriles, and the corresponding cyanodioxanes were obtained in satisfactory yields, except for two cases using styrene and 2-(5-methylfuryl)-substituted acylacetonitrile (R3 = 2-(5-methylfuryl)) (Scheme 14) [106].

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