铜烯碳酰胺：通过重氮烯醛和 N-取代的吡咯之间的 [4+2] 苯并annulation 快速获得 1,7-二取代的吲哚

IF 1.4 4区化学 Q3 CHEMISTRY, ORGANIC Tetrahedron Letters Pub Date : 2024-11-13 Epub Date: 2024-10-19 DOI:10.1016/j.tetlet.2024.155331

Bapurao Sudam Lad, Pratap Kumar Mandal, Rahul Chakrawarti, Sreenivas Katukojvala

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引用次数: 0

摘要

这里首次公开了一种具有高度亲电性的铜烯碳化合物，它具有类羰基化合物的反应活性。在铜催化下，重氮烯醛和 N-取代的吡咯直接合成 1,7-二取代吲哚的过程中，证明了瞬时铜烯碳烯酮的合成用途。在该反应中，Cu-烯碳化合物作为 4[C] 双亲电合成体，而吡咯作为 2[C] 双亲核体，导致 [4+2] 苯并反应。

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Copper-enalcarbenoids: Rapid access to 1,7-disubstituted indoles via [4+2] benzannulation between diazoenals and N-substituted pyrroles

A highly electrophilic copper enalcarbenoid has been disclosed here for the first time for its carbenoid reactivity. The synthetic utility of the transient Cu-enalcarbenoids has been demonstrated in the Cu-catalyzed direct synthesis of 1,7-disubstituted indoles from diazoenals and N-substituted pyrroles. In this reaction, Cu-enalcarbenoid served as a 4[C] biselectrophilic synthon whereas pyrrole served as a 2[C] bisnucleophilie leading to [4+2] benzannulation.

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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.