A convenient Y(OTf)3-catalyzed cascade formal [4 + 2] cyclization approach for the formation of 1,4-benzoxazine scaffolds from benzoxazoles and propargyl alcohols through a ring-opening and regioselective ring-closure process has been… Click to show full abstract
A convenient Y(OTf)3-catalyzed cascade formal [4 + 2] cyclization approach for the formation of 1,4-benzoxazine scaffolds from benzoxazoles and propargyl alcohols through a ring-opening and regioselective ring-closure process has been developed. By using this mild and practical protocol, a broad range of aldehyde-containing 1,4-benzoxazine compounds were prepared in moderate to excellent yields with good functional group tolerance. Mechanistic studies indicated that an SN1 nucleophilic substitution of benzoxazole with a propargyl cation was involved in this transformation.
Journal Title: Chemical communications
Year Published: 2022
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