DTBP mediated tandem oxidative reaction of o-aminobenzamides with alcohols for the synthesis of quinazolinones

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2025-05-05 DOI:10.1080/00397911.2025.2500050

Jin Li (Investigation Writing – original draft) , Haotian Cao (Investigation Methodology) , Hongyou Tian (Data curation Investigation) , Huaju Li (Data curation) , Yongke Hu (Funding acquisition Project administration Writing – review & editing)

引用次数: 0

Abstract

A practical and efficient methodology for the construction of quinazolinones from readily available alcohols and o-aminobenzamides in the presence of DTBP/Cu(OTf)₂ has been developed. This catalytic system exhibits good functional group tolerance and could afford a range of quinazolinones in good to excellent yields. In case of gram-scale reaction, 2-phenylquinazolin-4(3H)-one (3a) was obtained in 86% isolated yield, which indicated this protocol was amenable to scale up and had a potential value in industry. In addition, a plausible reaction mechanism involving a radical process has been proposed, and further applications of this catalytic system are under way in our laboratory.

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邻氨基苯醚介导邻氨基苯酰胺与醇的串联氧化反应合成喹唑啉酮

在DTBP/Cu(OTf)2的存在下，建立了一种实用而高效的以易得的醇和邻氨基苯酰胺为原料合成喹唑啉酮的方法。该催化体系具有良好的官能团耐受性，并能以优异的收率生产一系列喹唑啉酮。在克级反应中，2-苯基喹唑啉-4(3H)- 1 （3a）的分离收率为86%，表明该工艺具有扩大生产规模的可行性和潜在的工业应用价值。此外，还提出了一种涉及自由基过程的合理反应机理，并在我们的实验室中进行了进一步的应用。

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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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.