Amidation of amino aryl acids with orthoesters in aqueous ammonium hydroxide: A strategy to construct quinazolinones and pyrido[2,3-d]pyrimidinones

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-09-13 DOI:10.1016/j.tet.2025.134940

Subrata Barick, Sandeep Chandrashekharappa

引用次数: 0

Abstract

A one-pot oxidative cyclization of 2-amino aryl acids with orthoesters to quinazoline-4(3H)-ones and pyrido[2,3-d]pyrimidinones was described in a greener approach using aqueous ammonium hydroxide. The synthetic protocol enables greater selectivity with synthetic utility. A wide range of substrate scope was explored with good to excellent yields. The reaction mechanism involves N-benzylation/alkylation, amidation, and subsequent oxidative annulation.

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氨基芳基酸与正位酯在氢氧化铵水溶液中的酰胺化：一种构建喹唑啉酮和吡啶[2,3-d]嘧啶酮的策略

采用一种更环保的方法，用氢氧化铵水溶液将2-氨基芳基酸与邻苯二甲酸酯一锅氧化环化成喹唑啉-4（3H）酮和吡啶[2,3-d]嘧啶酮。合成协议使合成工具具有更大的选择性。探索了广泛的衬底范围，并获得了良好的收率。反应机理包括n -苄基化/烷基化、酰胺化和随后的氧化环化。

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

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.