吡啶二炔前体的合成与应用
首发时间:2019-04-11
摘要:本论文设计合成了一种新型吡啶二炔前体4-叔丁基二甲基硅基-3,5-二三氟甲磺酸吡啶基酯。以3,5-二氯吡啶为原料,经6步反应可以得到该吡啶二炔前体。其结构经红外,核磁及高分辨质谱进行了表征。对该吡啶二炔前体的反应活性进行测试,其可以与呋喃发生[4+2]反应,与硫代苯甲酰胺类化合物发生3,4-双亲核反应,与苯磺酰胺类化合物发生3,5-二胺基化反应。通过这些反应活性实验,成功实现了吡啶环上的连续三官能化转化,打破了过去简单吡啶炔只能实现邻位双取代反应的限制。
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The synthesis of pyridiyne and its application
Abstract:In this paper, a novel pyridiyne precusor, 4-t-butyldimethylsilyl-3,5-ditriflate-pyridine, is designed and synthetized. The pyridiyne precusor can be obtained by a 6-step reaction using 3,5-dichloropyridine as a raw material, and its structure is characterizedby IR, NMR and HRMS. The reactivity of the pyridiyne precursor is tested, which can undergo a [4+2] cycloaddition reaction with furan, a 3,4-dinucleophilic reaction with thiobenzamide, and a 3,5-diamination reaction with benzenesulfonamide. Through these experiments, continuous trifunctionalization of the pyridine ring was successfully achieved, breaking the limitation that the simple pyridinye can only achieve the orhth-difunctionalization in one reaction.
Keywords: Aryne Pyridyne Pyridiyne Muilt-functionalization
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