Mild and efficient construction of nitrogen-containing heterocycles from ortho-ethynylbenzaldehydes and anilines

Abstract

A mild and transition-metal-free strategy for the synthesis of isoindolin-1-imines and isoquinolinium salts has been developed using ortho-ethynylbenzaldehydes and anilines. HFIP was employed as an effective promoter, facilitating nucleophilic addition and annulation to afford diverse isoindolin-1-imines in good yields. Alternatively, isoquinolinium salts were obtained by addition of ammonium iodide. Both reactions exhibited broad functional group tolerance and were successfully applied on gram scales as well as for further transformation, providing a practical strategy in pharmaceutical development and organic synthesis.

Graphical abstract: Mild and efficient construction of nitrogen-containing heterocycles from ortho-ethynylbenzaldehydes and anilines

Supplementary files

Article information

Article type
Paper
Submitted
17 Apr 2025
Accepted
25 Jun 2025
First published
27 Jun 2025

Org. Biomol. Chem., 2025, Advance Article

Mild and efficient construction of nitrogen-containing heterocycles from ortho-ethynylbenzaldehydes and anilines

J. Zhao, H. Qian, Y. Zi, S. Ji and X. Xu, Org. Biomol. Chem., 2025, Advance Article , DOI: 10.1039/D5OB00634A

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