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A facile synthesis of pyrano[2,3‐d:6,5‐d′]dipyrimidines via microwave‐assisted multicomponent reactions catalyzed by β‐cyclodextrin
Journal of Heterocyclic Chemistry ( IF 2.4 ) Pub Date : 2020-12-12 , DOI: 10.1002/jhet.4207
Jayashree Avvadukkam 1 , Narayana Badiadka 1 , Sarojini B. Kunhanna 2 , Madan S. Kumar 3
Affiliation  

A facile three‐component reaction of aromatic aldehyde, 2,2‐dimethyl‐1,3‐dioxane‐4,6‐dione, and 6‐amino‐1,3‐dimethyluracil was developed for the first time using β‐cyclodextrin (β‐CD) as a macrocyclic host for aldehyde and an efficient catalyst that leads to a batch of novel pyrano[2,3‐d:6,5‐d′]dipyrimidines (4a‐k). The synthesis was accomplished with the aid of microwave irradiations in solvent‐free conditions. The product obtained was in contrast to the previous report in which a similar reaction resulted in a mixture of benzylidenepyrimidine and bisaminopyrimidine analogs in the presence of triethylbenzylammonium chloride in an aqueous medium. The formation of the pyrano[2,3‐d:6,5‐d′]dipyrimidines may be in virtue of the property of β‐CD to construct new CC and CX (where X = heteroatom) bonds. Reusability of the catalyst up to three runs without any noteworthy change in catalytic activity is one of the main features of the reaction. Other noteworthy features are good to excellent yields, eco‐friendly procedure, non‐column chromatographic purification, and mild conditions.

中文翻译:

β-环糊精催化微波辅助多组分反应轻松合成吡喃并[2,3-d:6,5-d']双嘧啶

首次使用β-环糊精(β -CD)作为醛的大环主体和高效催化剂,可产生一批新颖的吡喃并[2,3- d:6,5- d ']双嘧啶(4a-k)。合成是在无溶剂条件下借助微波辐射完成的。所得产物与先前的报道相反,在先前的报道中,类似的反应在水性介质中在三乙基苄基氯化铵的存在下产生了亚苄基嘧啶和双氨基嘧啶类似物的混合物。吡喃并[2,3- d:6,5- d′]双嘧啶可能是依靠β-CD的特性来构建新的CCCX(其中X =杂原子)键。该催化剂的最多可重复使用三次,而催化活性没有任何显着变化是反应的主要特征之一。其他值得注意的功能还包括优异的产量,环保的操作流程,非色谱柱色谱纯化和温和的条件。
更新日期:2020-12-12
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