Copper promoted synthesis of substituted quinolines from benzylic azides and alkynes
作者:Ching-Zong Luo、Parthasarathy Gandeepan、Yun-Ching Wu、Wei-Chen Chen、Chien-Hong Cheng
DOI:10.1039/c5ra23065a
日期:——
novel copper promoted synthesis of substituted quinolines from various benzylic azides and internal alkynes has been demonstrated. The reaction features a broad substrate scope, high product yields and excellent regioselectivity. In contrast to the known two-step process of acid promoted [4 + 2] cycloaddition reaction and oxidation, the present methodology allows the synthesis of quinolines in a single
已经证明了一种新颖的铜促进的由各种苄基叠氮化物和内部炔烃合成取代喹啉的方法。该反应具有广泛的底物范围,高产物收率和优异的区域选择性。与酸促进[4 + 2]环加成反应和氧化的已知两步方法相比,本方法可在中性反应条件下一步合成喹啉,并可用于合成具有生物活性的6-氯-2,3-二甲基-4-苯基喹啉(抗寄生虫剂)和3,4-二苯基喹啉-2(1 H)-one(p38αMAP激酶抑制剂)。可能的反应机理涉及将叠氮化苄重排至N-芳基丙氨酸(Schmidt反应),然后与内部炔烃进行分子间[4 + 2]环加成反应。