聚磷酸酯促进了 2-氨基苯甲腈喹唑啉-4(3H)-亚胺的合成。

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

The Journal of Organic Chemistry Pub Date : 2024-10-04 Epub Date: 2023-03-15 DOI:10.1021/acs.joc.2c02558

Natalia B Kilimciler, Nicolás M Palavecino, Nadia Gruber, Daniel R Vega, Liliana R Orelli, Jimena E Díaz

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引用次数: 0

摘要

报告了一种通过三甲基硅基聚磷酸盐（PPSE）促进 2-氨基苯甲腈与仲酰胺反应合成喹唑啉-4(3H)-亚胺（QIs）的新方法。该反应具有通用性，可合成具有可变 2-取代基的 N3-芳基和 N3-烷基 QIs，产量高。该反应还可扩展到含有其他官能团的衍生物。该方法操作简单，使用容易获得的起始材料和温和的脱水剂，对官能团有广泛的耐受性。事实证明，该反应过程适用于扩大规模。根据文献数据和实验观察结果，提出了通过中间体亚硝基离子进行反应的可能途径。

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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Polyphosphoric Acid Esters Promoted Synthesis of Quinazolin-4(3H)-imines from 2-Aminobenzonitrile.

A novel method for the synthesis of quinazolin-4(3H)-imines (QIs) by trimethylsilyl polyphosphate (PPSE) promoted reaction of 2-aminobenzonitrile with secondary amides is reported. The reaction is general and allows for the synthesis of N³-aryl and N³-alkyl QIs with variable 2-substituents affording high yields. The procedure was extended to derivatives bearing additional functional groups. The method is operationally simple, involves easily available starting materials and a mild dehydrating agent, with wide functional group tolerance. The reaction procedure proved to be suitable for scaling-up. A possible reaction path via an intermediate nitrilium ion is proposed on the basis of literature data and experimental observations.

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来源期刊

The Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.