Diastereoselective Synthesis of Highly Functionalized γ-Lactams via Ugi Reaction/Michael Addition.

IF 3.5 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal Pub Date : 2025-01-02 Epub Date: 2024-11-09 DOI:10.1002/asia.202400917

Herika D A Vidal, Paulo S G Nunes, Alice K A Martinez, Marcelo A P Januário, Pedro H O Santiago, Javier Ellena, Arlene G Corrêa

引用次数: 0

Abstract

The γ-lactam ring is a prominent feature in medicinal chemistry, and its synthesis has garnered significant interest due to its valuable properties. Among the γ-lactams, 2-oxopyrrolidine-3-carbonitrile derivatives stand out as versatile synthons that can be readily transformed into a variety of other functional groups. In this work, we successfully synthesized highly functionalized 3-cyano-2-pyrrolidinones with moderate to good overall yields using the Ugi reaction followed by intramolecular Michael addition. The process demonstrated excellent diastereoselectivity and showed good tolerance to a range of isonitriles and carbonyl compounds.

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通过乌基反应/迈克尔加成法非对映选择性合成高功能化 γ-内酰胺。

γ-内酰胺环是药物化学中的一个突出特征，由于其宝贵的特性，其合成引起了极大的兴趣。在γ-内酰胺类化合物中，2-氧代吡咯烷-3-甲腈衍生物是一种多用途合成物，可以很容易地转化为其他多种官能团。在这项工作中，我们利用 Ugi 反应和分子内迈克尔加成法成功合成了高官能度的 3-氰基-2-吡咯烷酮，总产率达到中等至良好水平。该过程具有出色的非对映选择性，并对一系列异腈和羰基化合物具有良好的耐受性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Chemistry - An Asian Journal 化学-化学综合

CiteScore

7.00

自引率

2.40%

发文量

535

审稿时长

1.3 months

期刊介绍： Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).