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Updated: Jul 12, 2025

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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多米诺三组分N-乙化/[4 + 2] 循环添加/多基替代的烯合成[f]异醇-4-碳酸酸

Kseniya A Alekseeva1, Maryana A Nadirova1, Vladimir P Zaytsev1

  • 1Department of Organic Chemistry, RUDN University, Miklukho-Maklaya str. 6, 117198 Moscow, Russian Federation.

The Journal of organic chemistry
|October 23, 2023
PubMed
概括

一种新的三组分反应有效合成具有高立体选择性的[f]异醇衍生物. 分子内维尼拉烯循环添加 (IMDAV) 被确定为限制速率的步骤.

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
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