Brønsted-acid-mediated cyclocondensation towards dihydro-1-benzazepines

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-04-10 DOI:10.1016/j.tetlet.2025.155572

Letian Xu, Alena M. Vasquez, Jose M. Medina, Juntao Sun, Keary M. Engle

引用次数: 0

Abstract

A Brønsted-acid-mediated cyclocondensation of 2-alkenylanilines and (hetero)arylethanones to access dihydro-1-benzazepines is reported. Various 2-alkenylanilines and electron-deficient (hetero)arylethanones are tolerated and afford moderate to good yields. Coordination of 2-pyridinyl-substituted dihydro-1-benzazepines to palladium(II) demonstrates their ability to serve as novel N,N-bidentate ligand scaffolds. Isotope labeling and reactivity trends are consistent with an aza-8π-electrocyclization mechanism for this medium-sized ring-forming reaction.

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br ønsted-酸介导的二氢-1-苯二氮卓类化合物的环缩合反应

报告了一种由勃氏酸介导的 2-烯基苯胺和（杂）芳基乙酮的环缩合反应，从而获得二氢-1-苯并氮杂卓。各种 2-烯基苯胺和缺电子的（杂）芳烷酮均可耐受，并可获得中等到良好的产率。2 吡啶基取代的二氢-1-苯并氮杂卓与钯（II）的配位证明了它们作为新型 N,N-配位体支架的能力。同位素标记和反应趋势与这种中型成环反应的氮杂-8π-电环化机理一致。

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.