Synthesis of chalcogen-functionalized 4H-chromen-4-ones via cyclization/chalcogenation of alkynyl aryl ketones mediated by Selectfluor®

Thiago Anjos; Elba L. Gutterres; Daniela A. Barancelli; Roberta Cargnelutti; Benhur Godoi; Thiago Barcellos; Ricardo F. Schumacher

doi:10.1039/D2NJ05567H

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Synthesis of chalcogen-functionalized 4H-chromen-4-ones via cyclization/chalcogenation of alkynyl aryl ketones mediated by Selectfluor®†

Thiago Anjos,^a Elba L. Gutterres,^a Daniela A. Barancelli,*^b Roberta Cargnelutti,

^a Benhur Godoi,

^c Thiago Barcellos^d and Ricardo F. Schumacher

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Federal University of Santa Maria – UFSM, Santa Maria, RS, Brazil
E-mail: ricardo.schumacher@ufsm.br

^b Department of Chemistry, Federal University of Technology – Paraná (UTFPR), Campo Mourão, PR, Brazil
E-mail: dbarancelli@utfpr.edu.br

^c Programa de Pós-Graduação em Ambiente e Tecnologias Sustentáveis, Núcleo de Síntese, Aplicação e Análise de Compostos Orgânicos e Inorgânicos, Federal University of Fronteira Sul – UFFS, Cerro Largo, RS, Brazil

^d Laboratory of Biotechnology of Natural and Synthetic Products, University of Caxias do Sul (UCS), Caxias do Sul, RS, Brazil

Abstract

The synthesis of organochalcogen-functionalized chromenones starting from diorganyl dichalcogenides and alkynyl aryl ketones has been developed. Selectfluor® mediates these cyclization/organochalcogenation reaction sequences under mild and open-to-air conditions. The six-membered heterocycles were obtained via a selective 6-endo-dig cyclization compatible with the use of both diorganyl diselenides and disulfides. This synthetic methodology still proved to be versatile to synthesize organochalcogen-substituted thiochromenone and isocromenone derivatives.

This article is part of the themed collection: 50th anniversary of ICCST: celebrating ICCST at its 15th Edition

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DOI: https://doi.org/10.1039/D2NJ05567H
Article type: Paper
Submitted: 13 Nov 2022
Accepted: 10 Dec 2022
First published: 12 Dec 2022

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New J. Chem., 2023,47, 1076-1080

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Synthesis of chalcogen-functionalized 4H-chromen-4-ones via cyclization/chalcogenation of alkynyl aryl ketones mediated by Selectfluor®

T. Anjos, E. L. Gutterres, D. A. Barancelli, R. Cargnelutti, B. Godoi, T. Barcellos and R. F. Schumacher, New J. Chem., 2023, 47, 1076 DOI: 10.1039/D2NJ05567H

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New Journal of Chemistry

Synthesis of chalcogen-functionalized 4H-chromen-4-ones via cyclization/chalcogenation of alkynyl aryl ketones mediated by Selectfluor®†

Abstract

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Article information

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Synthesis of chalcogen-functionalized 4H-chromen-4-ones via cyclization/chalcogenation of alkynyl aryl ketones mediated by Selectfluor®

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