以乙醇为乙烷替代物，通过AIBN/二硫代酸促进亚胺的序贯氧化自由基α-羟甲基化/环化获得2-芳基喹啉

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-08-13 DOI:10.1016/j.tetlet.2025.155792

Kui Zheng , Hailong Chen , Yang Zhao , Junhao Peng , Xinyang Jiang , Zhenlian Wang , Jiang Cheng

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引用次数: 0

摘要

在氢亚硫酸钠/ aibn催化的2-芳基喹啉多组分反应中，乙醇代替二恶烷、碳酸乙烯或丙烯酸作为乙烷替代物。这个过程可能始于α-羟基碳中心的亲核自由基在二亚硫酸钠和氧存在下的形成。然后进行原位亚胺α-羟甲基化，消除1个等价物H2O， 6 π电环化和芳构化反应。因此，这种无金属的程序代表了一种可持续和有效的途径来获得一系列2-芳基喹啉。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Accessing 2-aryl quinolines via AIBN/dithionite-promoted sequential oxidative radical α-hydroxymethylation/cyclization of imine employing ethanol as ethyne surrogate

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Accessing 2-aryl quinolines via AIBN/dithionite-promoted sequential oxidative radical α-hydroxymethylation/cyclization of imine employing ethanol as ethyne surrogate

Ethanol, rather than dioxane, vinylene carbonate, or acrylic acid, acted as the ethyne surrogate in sodium hydrosulfite/AIBN-promoted multicomponent reactions (MCRs) involving amines and aldehydes toward 2-aryl quinolines under O₂ atmosphere. This procedure likely started with the formation of α-hydroxy carbon centered nucleophilic radical in the presence of sodium dithionite and O₂. Then the reaction proceeded with sequential oxidative radical α-hydroxymethylation of in situ-formed imine, elimination of one equivalent of H₂O, and 6 π electrocyclization followed by aromatization. As such, this metal-free procedure represents a sustainable and efficient pathway to access a series of 2-aryl quinolines.

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.