Issue 13, 2024

Gold-catalyzed intermolecular tandem cyclization/[4 + 3] cycloaddition of 2-(1-alkynyl)-cyclopropyl pyridines with nitrones: an efficient strategy for the synthesis of [1,2]oxazepino[5,4-a] indolizines

Abstract

A new and efficient approach is described for the diastereoselective synthesis of [1,2]oxazepino[5,4-a] indolizines via a gold-catalyzed [4 + 3] cycloaddition reaction of 2-(1-alkynyl)-cyclopropyl pyridine with nitrones. This methodology has great potential to construct seven-membered heterocycle-fused indolizine scaffolds from simple building blocks. Based on our preliminary results, a probable mechanism for this reaction pathway has been proposed.

Graphical abstract: Gold-catalyzed intermolecular tandem cyclization/[4 + 3] cycloaddition of 2-(1-alkynyl)-cyclopropyl pyridines with nitrones: an efficient strategy for the synthesis of [1,2]oxazepino[5,4-a] indolizines

Supplementary files

Article information

Article type
Research Article
Submitted
31 Mar 2024
Accepted
15 May 2024
First published
16 May 2024

Org. Chem. Front., 2024,11, 3685-3691

Gold-catalyzed intermolecular tandem cyclization/[4 + 3] cycloaddition of 2-(1-alkynyl)-cyclopropyl pyridines with nitrones: an efficient strategy for the synthesis of [1,2]oxazepino[5,4-a] indolizines

F. Rao, M. Cheng, Z. Hu, X. Chen, S. Zhao and Z. Chen, Org. Chem. Front., 2024, 11, 3685 DOI: 10.1039/D4QO00580E

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