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Synthesis 2025; 57(23): 3599-3605
DOI: 10.1055/a-2680-2438
Paper

Xanthate-Based Radical Addition/Spirocyclization on C2-Substituted Tryptamine-Derived Isonitriles

Authors

  • Enrique Becerril-Rodríguez

    1   Instituto de Química, Universidad Nacional Autónoma de México, Ciudad de México, México (Ringgold ID: RIN7180)

  • Mario Castañón-García

    1   Instituto de Química, Universidad Nacional Autónoma de México, Ciudad de México, México (Ringgold ID: RIN7180)

  • Luis D. Miranda 

    1   Instituto de Química, Universidad Nacional Autónoma de México, Ciudad de México, México (Ringgold ID: RIN7180)

Funding Information Financial support from CONAHCYT (Project CBF2023-2024-2227) is gratefully acknowledged.
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Graphical Abstract

Abstract

A metal-free protocol for constructing spiroindolines via a radical cascade process is reported. The reaction cascade comprises a radical intermolecular addition to a tryptamine-derived isonitrile, followed by spirocyclization of the intermediate radical onto the C-3 position of the indole system, and concluding with a final oxidation step. Introducing a malonyl or acetoxyl group at the C-2 position of the indole system, along with the addition of a radical bearing an electron-withdrawing group, facilitated the formation of the enamine products. The use of the xanthate-mediated chemistry enabled the generation of primary and secondary electrophilic radicals derived from esters, nitriles, ketones, and lactones.

Keywords

Spiroindolines - Isonitriles - Free radicals - Xanthates - Dienamines

Supplementary Material



Publication History

Received: 08 May 2025

Accepted after revision: 08 August 2025

Accepted Manuscript online:
08 August 2025

Article published online:
09 September 2025

© 2025. Thieme. All rights reserved.

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany

 

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