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DOI: 10.1055/a-2752-7839
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Recent Advances in Cyclization Reactions of 1,5-Enynones and 1,6-Enynones

Authors

  • Saideh Rajai-Daryasarei

    1   School of Chemistry, College of Science, University of Tehran, Tehran, Iran (Ringgold ID: RIN48425)
    2   Peptide Chemistry Research Institute, K. N. Toosi University of Technology, Tehran, Iran (Ringgold ID: RIN108871)

  • Vaezeh Fathi Vavsari 

    2   Peptide Chemistry Research Institute, K. N. Toosi University of Technology, Tehran, Iran (Ringgold ID: RIN108871)

  • Elmira Jamshidi

    2   Peptide Chemistry Research Institute, K. N. Toosi University of Technology, Tehran, Iran (Ringgold ID: RIN108871)

  • Saeed Balalaie 

    2   Peptide Chemistry Research Institute, K. N. Toosi University of Technology, Tehran, Iran (Ringgold ID: RIN108871)

Supported by: Alexander von Humboldt Foundation
We gratefully acknowledge INSF (Iran National Science Foundation, Grant No. 99029802) for the financial support. S. B. Thanks Alexander von Humboldt Foundation for the research fellowship.
Supported by: Iran National Science Foundation 99029802
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Graphical Abstract

Abstract

The alkyne functional group and a,ß-unsaturated carbonyl compounds serve as key building blocks for assembling fused aromatic and heterocyclic structures. The placement of these two functional groups at the ortho positions on a benzene ring provides an opportunity to design diverse reactions and access a wide variety of aromatic compounds. By using appropriate catalysts, radical initiators, nucleophiles, or electrochemical circumstances, the selectivity and specificity of the reaction can be precisely controlled, leading to the formation of C–C and C–heteroatom bonds and selective cyclization. Various organic scaffolds, including indenones, benzofurans, naphthoquinones, benzofluorenones, and isochromenes, can be efficiently produced through these transformations. This review provides readers with a detailed understanding of how catalysts and reaction circumstances affect the regioselectivity and stereoselectivity of ynenone reactions, thereby enabling them to choose the best reaction routes.

Keywords

Alkyne - Electrochemistry - Radical reaction - Heterocycles - Cyclization - β-Unsaturated carbonyl compounds


Publication History

Received: 29 October 2025

Accepted after revision: 20 November 2025

Accepted Manuscript online:
21 November 2025

Article published online:
20 January 2026

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