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Isocyanide-based consecutive Bargellini/Ugi reactions: an efficient method for the synthesis of pseudo-peptides containing three amide bonds
Amino Acids ( IF 3.0 ) Pub Date : 2020-11-27 , DOI: 10.1007/s00726-020-02917-1
Hassan Farhid 1 , Mohammad Taghi Nazeri 1 , Ahmad Shaabani 1 , Mahsa Armaghan 2 , Christoph Janiak 2
Affiliation  

Isocyanide-based consecutive Bargellini/Ugi multicomponent reactions as a combinatorial strategy have been developed for the synthesis of new class of pseudo-peptides. Via Bargellini reaction 3-carboxamido-isobutyric acids are prepared using acetone, chloroform, sodium hydroxide, and isocyanides. Then, using Ugi multicomponent reaction strategy, pseudo-peptides containing three amide bonds are synthesized using the Bargellini reaction product, aldehydes, amines, and isocyanides. This is an efficient and eco-friendly approach for easy access to wide variety of structurally diverse, drug-like pseudo-peptides from cheap and readily available precursors in high yields.



中文翻译:

基于异氰化物的连续 Bargellini/Ugi 反应:一种合成含有三个酰胺键的假肽的有效方法

已经开发出基于异氰化物的连续 Bargellini/Ugi 多组分反应作为一种组合策略,用于合成新型假肽。通过 Bargellini 反应,使用丙酮、氯仿、氢氧化钠和异氰化物制备 3-甲酰胺基异丁酸。然后,使用 Ugi 多组分反应策略,使用 Bargellini 反应产物、醛、胺和异氰化物合成含有三个酰胺键的假肽。这是一种高效且环保的方法,可以轻松地从廉价且容易获得的前体中以高产率获得各种结构多样的类药物假肽。

更新日期:2020-11-27
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