Preparation Of Aryl Nitriles And Their Application In The Synthesis Of Quindolines

Since the great importance of aryl nitriles, this dissertation mainly discusses the synthesis of aryl nitriles and their application in the synthesis of quindoline derivatives.In part1, we use aryl boronic acids and benzyl cyanide to synthesize aryl nitriles. Compared to the previous cyanation of aryl boronic acids, this method has several advantages on easily available reactants, simple conditions and relatively low toxicity. It also has wide substrate scope with good yields, when the substrates are substituted with electron-donating groups, electron-withdrawing groups and steric hindrance groups. The mechanism experiments show the aryl iodides are reaction intermediates, which indicates that aryl boronic acids undergo iodination reaction followed by cyanation reaction.In part2, we synthesize the quindoline derivatives from2-cyano-N-triphenylphosphoranylidene anilines and a-diazoketones. Previous works are often with tedious steps, low yields and hard conditions. But this approach can undertake without any catalysts or additives in moderate yields. Then we study the photophysical property of quindoline derivatives. We find that methoxy group substituted quindoline derivative has good fluorescence quantum efficiency, promoting us to its application in detection of explosive TNT.