Electronic effect-controlled cyclizations for the synthesis of isoquinoline-fused oxazabicycles

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-07-25 DOI:10.1016/j.tetlet.2025.155770

Vijayabhaskar Bandaru , Sameer Vyasamudri , Jyothi Dhuguru , Vinod Jadhav , Ding-Yah Yang , Siddaiah Vidavalur

引用次数: 0

Abstract

We report an efficient synthesis of isoquinoline-derived 2,8-oxazabicycles through the coupling of 1-methyl-3,4-dihydroisoquinolines with 3-electron-withdrawing-substituted coumarins in toluene under refluxed conditions, without the need for external reagents. This domino reaction is primarily governed by the electronic properties of the reactants. The reaction mechanism is proposed to follow a sequence of Michael addition, lactone ring-opening, and intramolecular cyclization.

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电子效应控制环化合成异喹啉熔合恶氮杂环

我们报道了在回流条件下，通过1-甲基-3,4-二氢异喹啉与3-电子抽离取代香豆素在甲苯中偶联，在不需要外部试剂的情况下，有效地合成了异喹啉衍生的2,8-恶氮杂环。这种多米诺骨牌反应主要是由反应物的电子性质决定的。该反应机理为迈克尔加成、内酯开环和分子内环化。

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 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.