通过对含有乙烯基单腈的吡咯进行序贯亲核-亲电修饰合成1,5-二氢- 2h -吡咯-2-酮的新方法

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-08-18 DOI:10.1016/j.tetlet.2025.155795

Mikhail Yu. Belikov, Sergey A. Blinov

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引用次数: 0

摘要

本文报道了通过对2-（2-氧-1,2-二氢- 3h -吡咯-3-乙基）丙二腈进行顺序双亲核-亲电修饰，首次一锅合成1,5-二氢- 2h -吡咯-2-酮。该过程开始于在吡咯环C5原子上选择性地加入胺的亲核反应。这种关键的c5区域选择性首次被二维核磁共振光谱证实。胺的加成在C(CN) 2片段上产生亲核中心，使其随后与亲电的烷基卤化物反应。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Novel approach to the synthesis of 1,5-dihydro-2H-pyrrol-2-ones via sequential nucleophilic-electrophilic modification of pyrroles bearing a ylidenemalononitrile moiety

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Novel approach to the synthesis of 1,5-dihydro-2H-pyrrol-2-ones via sequential nucleophilic-electrophilic modification of pyrroles bearing a ylidenemalononitrile moiety

We report the first one-pot synthesis of 1,5-dihydro-2H-pyrrol-2-ones via sequential dual nucleophilic-electrophilic modification of 2-(2-oxo-1,2-dihydro-3H-pyrrol-3-ylidene)malononitriles. The process begins with regioselective nucleophilic addition of an amine to the pyrrole ring C5 atom. This key C5-regioselectivity was confirmed for the first time by 2D NMR spectroscopy. The amine addition generates a nucleophilic center at the C(CN)₂ fragment, allowing its subsequent reaction with electrophilic alkyl halides.

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.