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通过三个多组分反应合成含有二硫代氨基甲酸盐和 N,X-杂环基团的新型假肽。

Ensembling three multicomponent reactions for the synthesis of a novel category of pseudo-peptides containing dithiocarbamate and N,X-heterocylic groups.

机构信息

Department of Organic Chemistry, Faculty of Chemistry, Kharazmi University, P.O. Box 15719-14911, 49 Mofateh Street, Tehran, 31979-37551, Iran.

Institut für Chemie (IfC), Carl von Ossietzky Universität Oldenburg, P.O. Box 2503, 26111, Oldenburg, Germany.

出版信息

Amino Acids. 2019 Feb;51(2):263-272. doi: 10.1007/s00726-018-2661-0. Epub 2018 Oct 4.

Abstract

Consecutive multicomponent reactions have been applied for the synthesis of novel pseudo-peptides bearing dithiocarbamate and N,X-heterocyclic groups (X = S, O) in only one structure. The first multicomponent reaction includes the synthesis of dithiocarbamates using an amine or amino acid, CS and an electrophile. The second MCR is synthesis of Asinger imines using 2-chloroisobutyraldehyde, NaXH (X = S, O), ketone and ammonia. The final MCR is Ugi reaction to afford the corresponding three-dimensional pseudo-peptides. Various Asinger imines, carboxylic acids and isocyanides were applied in this protocol to provide diversities of pseudo-peptides in high to excellent yields.

摘要

连续多组分反应已被应用于新型含有二硫代氨基甲酸盐和 N,X-杂环基团(X = S,O)的假肽的合成,这些杂环基团仅在一个结构中存在。第一个多组分反应包括使用胺或氨基酸、CS 和亲电试剂合成二硫代氨基甲酸盐。第二个 MCR 是使用 2-氯异丁醛、NaXH(X = S,O)、酮和氨合成 Asinger 亚胺。最后一个 MCR 是 Ugi 反应,生成相应的三维假肽。该方案中应用了各种 Asinger 亚胺、羧酸和异氰化物,以高产率提供了多种假肽。

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