Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa.
Molecules. 2012 Nov 30;17(12):14186-204. doi: 10.3390/molecules171214186.
Iodine-methanol mediated oxidative-aromatization of 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)-ones afforded the corresponding 2-aryl-6,8-dibromo-4-methoxy-quinolines in high yield and purity. The isomeric 1-(2-amino-3,5-dibromophenyl)-3-aryl-2-propen-1-ones reacted with iodine in methanol afford in a single pot operation the corresponding 2-aryl-6,8-dibromo-4-methoxyquinoline (major) and 2-aryl-6,8-dibromoquinolin-4(1H)-one (minor) products that were separated in sequence by column chromatography on silica gel. Suzuki-Miyaura cross-coupling of the 6,8-dibromo-4-methoxyquinoline derivatives with excess arylvinylboronic acids afforded the corresponding 2-aryl-6,8-bis(2-arylethenyl)-4-methoxyquinolines. The absorption and fluorescence properties of these compounds were also determined.
碘-甲醇介导的 2-芳基-6,8-二溴-2,3-二氢喹啉-4(1H)-酮的氧化-芳构化反应以高产率和高纯度得到相应的 2-芳基-6,8-二溴-4-甲氧基喹啉。异 构的 1-(2-氨基-3,5-二溴苯基)-3-芳基-2-丙烯-1-酮与碘在甲醇中的反应在一锅操作中得到相应的 2-芳基-6,8-二溴-4-甲氧基喹啉（主要产物）和 2-芳基-6,8-二溴喹啉-4(1H)-酮（次要产物），它们通过硅胶柱色谱顺序分离。6,8-二溴-4-甲氧基喹啉衍生物与过量芳基乙烯基硼酸的铃木-宫浦交叉偶联反应得到相应的 2-芳基-6,8-双（2-芳基乙烯基）-4-甲氧基喹啉。还测定了这些化合物的吸收和荧光性质。
