An oxidative expansion mechanism of isatin-derived imines

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Chemical Sciences Pub Date : 2024-06-07 DOI:10.1007/s12039-024-02283-5

Mariana Umba-Erazo, Rodolfo Quevedo

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Abstract

Sodium borohydride induces the oxidative expansion of the imine derived from isatin and phenylethylamine to form 3-phenethylquinazoline-2,4(1H,3H)-dione. It has been proposed that this transformation occurs by in situ formation of hydroperoxyl anions by a reaction between sodium borohydride and atmospheric oxygen. To contribute to understanding this oxidative expansion, the reaction between the imine derived from isatin and phenylethylamine with hydrogen peroxide was studied in this work. From this reaction, 3-phenethylquinazoline-2,4(1H,3H)-dione was isolated and two by-products were identified: N-phenethyl-2-(3-phenethyl-ureido)-benzamide and methyl(2-(phenethylcarbamoyl)phenyl)carbamate. This article analyses the structure of these by-products and proposes a mechanism that explains the reaction.

Graphical abstract

It was established that the reaction of the imine derived from isatin and phenylethylamine with hydrogen peroxide produces a mixture of three compounds: 3-phenethylquinazoline-2,4(1H,3H)-dione, N-phenethyl-2-(3-phenethyl-ureido)-benzamide and methyl(2-(phenethylcarbamoyl)phenyl)carbamate. A reaction mechanism is proposed that explains this behaviour

Abstract Image

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靛红衍生亚胺的氧化扩展机制

硼氢化钠可诱导由异靛红和苯乙胺衍生的亚胺发生氧化膨胀，形成 3-苯乙基喹唑啉-2,4(1H,3H)-二酮。有人提出，这种转变是通过硼氢化钠与大气中的氧气反应在原位形成氢过氧阴离子而发生的。为了帮助理解这种氧化扩展，这项工作研究了由异靛红和苯乙胺衍生的亚胺与过氧化氢的反应。从该反应中分离出了 3-苯乙基喹唑啉-2,4(1H,3H)-二酮，并确定了两种副产物：N-苯乙基-2-(3-苯乙基-脲基)苯甲酰胺和(2-(苯乙基氨基甲酰基)苯基)氨基甲酸甲酯。本文分析了这些副产物的结构，并提出了解释该反应的机理。图解摘要已经确定，由异汀和苯乙胺衍生的亚胺与过氧化氢反应会产生三种化合物的混合物：3-苯乙基喹唑啉-2,4(1H,3H)-二酮、N-苯乙基-2-(3-苯乙基-脲基)苯甲酰胺和(2-(苯乙基氨基甲酰基)苯基)氨基甲酸甲酯。提出了解释这种行为的反应机理

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来源期刊

Journal of Chemical Sciences CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

3.10

自引率

5.90%

发文量

107

审稿时长

1 months

期刊介绍： Journal of Chemical Sciences is a monthly journal published by the Indian Academy of Sciences. It formed part of the original Proceedings of the Indian Academy of Sciences – Part A, started by the Nobel Laureate Prof C V Raman in 1934, that was split in 1978 into three separate journals. It was renamed as Journal of Chemical Sciences in 2004. The journal publishes original research articles and rapid communications, covering all areas of chemical sciences. A significant feature of the journal is its special issues, brought out from time to time, devoted to conference symposia/proceedings in frontier areas of the subject, held not only in India but also in other countries.