Issue 11, 2023

Nitrogen atom insertion into indenes to access isoquinolines

Abstract

We report a convenient protocol for a nitrogen atom insertion into indenes to afford isoquinolines. The reaction uses a combination of commercially available phenyliodine(III) diacetate (PIDA) and ammonium carbamate as the nitrogen source to furnish a wide range of isoquinolines. Various substitution patterns and commonly used functional groups are well tolerated. The operational simplicity renders this protocol broadly applicable and has been successfully extended towards the direct interconversion of cyclopentadienes into the corresponding pyridines. Furthermore, this strategy enables the facile synthesis of 15N labelled isoquinolines, using 15NH4Cl as a commercial 15N source.

Graphical abstract: Nitrogen atom insertion into indenes to access isoquinolines

Supplementary files

Article information

Article type
Edge Article
Submitted
19 déc. 2022
Accepted
14 févr. 2023
First published
23 févr. 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 2954-2959

Nitrogen atom insertion into indenes to access isoquinolines

P. Finkelstein, J. C. Reisenbauer, B. B. Botlik, O. Green, A. Florin and B. Morandi, Chem. Sci., 2023, 14, 2954 DOI: 10.1039/D2SC06952K

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