纳米氧化铜催化一锅法合成β-咔啉类化合物
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摘要
通过纳米氧化铜催化色氨酸酯与醛的环化-氧化串联反应,发展了一种快速有效合成1,3-二取代-β-咔啉衍生物的一步合成法.在温和的条件下,目标产物可以达到中等到优良的产率.该反应的特点是纳米氧化铜既作为催化剂促进成环,又作为氧化剂将四氢-β-咔啉氧化成β-咔啉,从而提高了反应效率.
Compounds containing β-carboline moiety have a variety of special biochemical and pharmacological activities. In order to explore the method for efficient synthesize β-carbolines,a novel method applied Pictet-Spengler cyclization and coupling oxidation in one-step was studied. Tryptophan esters and aromatic aldehydes were heated in N,N-Dimethylformamide via the promotion of nano CuO. Twenty-five compounds of 1,3-disubstituted-β-carbolines were obtained in moderate to excellent yield with subsequent isolation and purification. Attractive features of this method included simple operation,high efficiency and mild condition. Especially,nano CuO as catalyst and oxidant promoted cyclization and oxidation processes in creating β-carbolines motif.
Compounds containing β-carboline moiety have a variety of special biochemical and pharmacological activities. In order to explore the method for efficient synthesize β-carbolines,a novel method applied Pictet-Spengler cyclization and coupling oxidation in one-step was studied. Tryptophan esters and aromatic aldehydes were heated in N,N-Dimethylformamide via the promotion of nano CuO. Twenty-five compounds of 1,3-disubstituted-β-carbolines were obtained in moderate to excellent yield with subsequent isolation and purification. Attractive features of this method included simple operation,high efficiency and mild condition. Especially,nano CuO as catalyst and oxidant promoted cyclization and oxidation processes in creating β-carbolines motif.
引文
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[24]Yan Q.,Gin E.,Banwell M.G.,Willis A.C.,Carr P.D.,Eur.J.Org.Chem.,2017,82(8),4328-4335
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[26]Joseph D.P.,Stephen P.W.,Org.Lett.,2010,12(18),4086-4089
[27]Tang J.G.,Liu H.,Zhou Z.Y.,Liu J.K.,Syn.Comm.,2010,40(10),1411-1417
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