Shanghai Key Laboratory of Functional Materials Chemistry, Key Lab for Advanced Materials and School of Chemistry and Molecular Engineering, East China University of Science and Technology , Meilong Road 130, Shanghai 200237, China.
J Org Chem. 2017 Jul 7;82(13):7032-7039. doi: 10.1021/acs.joc.7b00937. Epub 2017 Jun 13.
A copper-catalyzed cascade reaction of alkynols and 2-azidobenzaldehydes has been achieved, giving 6H-isochromeno[4,3-c]quinoline in yields of 40-81%. This reaction provides a novel, concise strategy for rapidly constructing compounds with fused N- and O-containing heterocycles. In contrast to previously reported reactions of alkynols in which the first step is intramolecular cycloisomerization, the first step in this novel reaction of alkynols is entropically unfavorable intermolecular addition. The resulting hemiacetal intermediate then undergoes intramolecular cyclization and aromatization to afford the product.
炔醇和 2-叠氮苯甲醛的铜催化级联反应已经实现，以 40-81%的产率得到 6H-异苯并呋喃并[4,3-c]喹啉。该反应为快速构建具有融合的 N 和 O 杂环的化合物提供了一种新颖、简洁的策略。与先前报道的炔醇反应不同，该炔醇新反应的第一步是熵不利的分子间加成，而不是分子内环化。所得半缩醛中间体随后进行分子内环化和芳构化以得到产物。
