Synthetic and mechanistic studies of the multicomponent reaction of 2‑(phenylethynyl)benzaldehyde, primary amine and diphenylphosphine oxide†

IF 3.4 3区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Reaction Chemistry & Engineering Pub Date : 2024-09-11 DOI:10.1039/d4re00387j
Kármen Szabó, Zsolt Kelemen, Pál T. Szabó, Erika Bálint
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Abstract

The synthesis of potentionally biologically active phosphinoyl functionalized N‑(2‑(phenylethynyl)benzyl)amine, 1,2‑dihydro-isoquinoline and 2H‑isoindoline via multicomponent reaction of 2‑(phenylethynyl)benzaldehyde, amine and diphenylphosphine oxide is described for the first time. Depending on the catalyst and the conditions used, the same one-pot three-component reaction can selectively lead to the mentioned three different products. The formation of the cyclic products was investigated by a comprehensive catalyst screening, as well as by quantum chemical calculations. It was found that for the synthesis of phosphinoyl functionalized N‑(2‑(phenylethynyl)benzyl)amine, there is no need to use any catalyst. For the complete formation of isoquinoline ring containing phosphine oxide, zirconium(IV) chloride was the most efficient catalyst and the 2H-isoindol-1-ylphosphine oxide was synthesized selectively by silver acetate catalyst. Furthermore, dihydro-isoquinolin-1-ylphosphine oxide was converted into the thermodynamically more stable 2H-isoindol-1-ylphosphine oxide.
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2-(苯乙炔基)苯甲醛、伯胺和二苯基氧化膦的多组分反应的合成和机理研究†。
首次描述了通过 2-(苯乙炔基)苯甲醛、胺和二苯基氧化膦的多组分反应合成具有潜在生物活性的膦酰官能化 N-(2-(苯乙炔基)苄基)胺、1,2-二氢异喹啉和 2H-异吲哚啉。根据催化剂和使用条件的不同,同一单锅三组分反应可选择性地生成上述三种不同的产物。通过催化剂的全面筛选和量子化学计算,研究了环状产物的形成。研究发现,合成膦酰官能化 N-(2-(苯乙炔基)苄基)胺无需使用任何催化剂。要完全形成含有氧化膦的异喹啉环,氯化锆(IV)是最有效的催化剂,醋酸银催化剂可选择性地合成 2H-isoindol-1-ylphosphine oxide。此外,二氢-异喹啉-1-基氧化膦被转化为热力学上更稳定的 2H-异吲哚-1-基氧化膦。
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来源期刊
Reaction Chemistry & Engineering
Reaction Chemistry & Engineering Chemistry-Chemistry (miscellaneous)
CiteScore
6.60
自引率
7.70%
发文量
227
期刊介绍: Reaction Chemistry & Engineering is a new journal reporting cutting edge research into all aspects of making molecules for the benefit of fundamental research, applied processes and wider society. From fundamental, molecular-level chemistry to large scale chemical production, Reaction Chemistry & Engineering brings together communities of chemists and chemical engineers working to ensure the crucial role of reaction chemistry in today’s world.
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