摘要/Abstract

1，2-二氢喹啉是一类重要的化合物.通过对已有方法的改进，发展了一类从喹啉出发高效合成1，2-二氢喹啉的反应（产率50%～96%）.通过对一系列还原剂的筛选发现，当使用氰基硼氢化钠作为还原剂时，能有效克服已有方法中低转化率的问题，实现被活化的喹啉盐经还原去芳构化反应得到一系列N-烷氧羰基取代的1，2-二氢喹啉.需要指出的是，除3-位或4-位含有取代基的底物能得到单一的目标产物外，其他底物都会生成过度还原的四氢喹啉副产物，二氢喹啉与四氢喹啉比例均大于4：1.同时，该方法相较于文献中的方法操作简便，无须使用大大过量的氯甲酸酯，增强了反应的实用性.
关键词: 喹啉, 1,2-二氢喹啉, 去芳构化, 氰基硼氢化钠
An efficient conversion of quinolines to 1,2-dihydroquinolines (50%~96% yield) was developed via the modification of the known methods. It was found that using sodium cyanoborohydride as a reductant would overcome the low conversion often encountered in previous studies. A series of N-alkoxycarbonyl-1,2-dihydroquinolines were obtained through reduction of activated quinolium salts. Notably, with the exception of the 3-and 4-substituted substrates, a mixture of 1,2-dihydro-quinolines and the over reduced tetrahydroquinolines was obtained with the ratio over 4:1. Besides, compared to the established methods, an easy operation without using large excess of chloroformate further enhances practicability of the methodology.
Key words: quinoline, 1,2-dihydroquinoline, dearomatization, sodium cyanoborohydride


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