The aza-Diels-Alder reaction between cyclic imine and aza-ortho-quinone methide precursor to access polycyclic-fused tetrahydroquinazoline

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-04-15 DOI:10.1016/j.tet.2025.134665

Xiaoke Zhang , Lu He , Xuan Zhang , Mao Lin , Xiaojiang Huang , Lingjie Meng , Huawu Shao , Wei Jiao , Qianlu Xing

引用次数: 0

Abstract

The aza-Diels-Alder reaction of cyclic imine with N-(o-chloromethyl) aryl amide has been developed. This method provides a highly efficient one-step strategy for constructing diverse ring-fused tetrahydroquinazoline scaffolds, including indolopyrido-tetrahydroquinazoline and isoquinolino-tetrahydroquinazoline derivatives, under mild conditions. The reactions achieved yields ranging from 47 % to 92 %.

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环亚胺与偶氮-邻醌甲酰前体间的偶氮- diols - alder反应制备多环熔合四氢喹啉

我们开发了环状亚胺与 N-（邻氯甲基）芳基酰胺的杂氮-Diels-Alder 反应。该方法提供了一种高效的一步法策略，可在温和的条件下构建多种环融四氢喹唑啉支架，包括吲哚并吡啶并四氢喹唑啉和异喹啉并四氢喹唑啉衍生物。反应的产率从 47% 到 92%不等。

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.