Sustainable Strategy to Access Fused Chromenoquinoline Analogues via Doebner–Von Miller-Type Reaction and Mechanistic Insights

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2025-07-09 DOI:10.1002/ajoc.70106

Paranimuthu Panjacharam, Sabbasani Rajasekhara Reddy

引用次数: 0

Abstract

In this study, we report a metal- and oxidant-free synthesis of fused chromenoquinolines via an acetic acid-promoted Doebner–Von Miller-type reaction. This effective method allows substituted anilines to react with 4-chloro-2H-chromene-3-carbaldehydes in an eco-friendly way, facilitating the formation of new C─N and C─C bonds while building fused polycyclic heteroaromatic rings. This protocol is broadly applicable for the synthesis of diverse 6H-chromeno[4,3-b]quinolines, which serve as versatile scaffolds for the subsequent cross-coupling reactions and C(sp³)─H oxidation.

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通过Doebner-Von miller型反应和机理洞察获得融合铬喹啉类似物的可持续策略

在这项研究中，我们报道了一种通过醋酸促进的Doebner-Von miller型反应合成熔融铬喹啉的无金属和无氧化剂的方法。这种有效的方法允许取代苯胺以一种环保的方式与4-氯- 2h -铬-3-碳醛反应，促进新的C─N和C─C键的形成，同时建立融合的多环杂芳环。该方案广泛适用于各种6h -色基[4,3-b]喹啉的合成，作为后续交叉偶联反应和C（sp3）─H氧化的多功能支架。

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

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.