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Volume 4, Issue 1
  • ISSN: 2665-976X
  • E-ISSN: 2665-9778

Abstract

Background

From an industries and academic perspective, there is a need for a method for producing 3-nitro-4-aryl-2H-chromen-2-ones from aryl alkynoate esters that is both economic and environmental benign. In this context, superoxide ion-assisted radical cascade reaction can be an efficient and greener protocol.

Objective

Herein, we have demonstrated an unprecedented methylene blue (MB) visible light photocatalysis for the production of a series of 3-nitro-4-aryl-2H-chromen-2-ones from readily available aryl alkynoate esters and a nitrating agent in solution.

Methods

Synthesis of 3-nitro-4-aryl-2H-chromen-2-ones has been performed in the presence of aryl alkynoate ester, TBAN, DIPEA, solvent, catalyst and molecular oxygen under visible light irradiation at room temperature. The products were purified by column chromatography using silica gel, and the mixture of ethyl acetate/petroleum ether as an eluting solvent and characterized by IR, NMR and mass spectroscopic analysis.

Results

A series of aryl alkynoate esters were successfully nitrated into corresponding 3-nitro-4-aryl-2H-chromen-2-ones with good isolated yields by this protocol, in which the key NO-radicals formed by the action of superoxide ion (O−∙).

Conclusion

In contrast to the literature-reported methods of synthesis of 3-nitro-4-aryl-2H-chromen-2-ones, the process described here for making 3-nitro-4-aryl-2H-chromen-2-ones uses methylene blue visible light photocatalysis, is inexpensive, mild, does not require a metal precursor or high temperatures, and is successful when using the direct sunlight.

© 2024 Bentham Science Publishers
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2024-06-11
2025-04-13

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Superoxide Ion-Assisted Radical Cascade Reaction: Synthesis of 3-nitro-4-aryl-2H-chromen-2-ones from Aryl Alkynoate Esters under Methylene Blue Visible Light Photocatalysis
Journal of Photocatalysis 4, E110624230919 (2024); https://doi.org/10.2174/012665976X295034240529130434
/content/journals/photocat/10.2174/012665976X295034240529130434
/content/journals/photocat/10.2174/012665976X295034240529130434
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  • Article Type:     Research Article
Keyword(s): aryl alkynoate esters; nitro-radicals; nitrocoumarins; Photocatalysis; superoxide ion; visible-light

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