Ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate in the smiles rearrangement reaction: straightforward synthesis of amino acid derived quinolin-2(1H)-one enamines,Molecular Diversity

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Ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate in the smiles rearrangement reaction: straightforward synthesis of amino acid derived quinolin-2(1H)-one enamines
Molecular Diversity ( IF 3.9 ) Pub Date : 2023-02-08 , DOI: 10.1007/s11030-022-10560-z
Sirous Haghipour ₁ , Morteza Mehrdad ₁ , Samanesadat Hosseini ₂ , Ali Moazzam ₃ , Kourosh Rad-Moghadam ₁ , Mohammad Mahdavi ₃

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This paper describes the development of 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate compound as a heterocyclic enols containing a Michael acceptor so that it participates in an Ugi-type multicomponent condensation through a Smiles rearrangement in replacement of acid components. The new four-component containing 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate, aldehyde derivatives, amine derivatives and isocyanides process leads readily and efficiently to heterocyclic enamines. This report is an outstanding strategy for the preparation of new biologically structures containing peptidic or pseudo-peptidic with quinolin-2(1H)-one scaffolds.

Graphical abstract

中文翻译：

smiles重排反应中的4-羟基-2-氧代-1,2-二氢喹啉-3-甲酸乙酯：氨基酸衍生的喹啉-2(1H)-酮烯胺的直接合成

本文描述了 4-羟基-2-氧代-1,2-二氢喹啉-3-羧酸酯化合物作为含有 Michael 受体的杂环烯醇的开发，使其通过 Smiles 重排参与 Ugi 型多组分缩合反应，以取代酸成分。包含4-羟基-2-氧代-1,2-二氢喹啉-3-羧酸酯、醛衍生物、胺衍生物和异氰化物的新型四组分工艺可以轻松有效地生成杂环烯胺。该报告是利用喹啉-2(1 H )-one 支架制备含有肽或假肽的新生物结构的杰出策略。

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更新日期：2023-02-08

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