Sulfur‐Promoted, DABCO‐Catalyzed Reaction of β‐Nitrostyrenes with 4‐Hydroxycoumarins: Access to Furo[3,2‐ <i>c</i> ]chromen‐4‐ones

Abstract In this study, we report a simple and elegant method for the preparation of furo[3,2‐ c ]coumarins from the one‐pot, [3+2] annulations of β‐nitroalkenes with 4‐hydroxycoumarins in the presence of sulfur and DABCO as the catalyst. This method utilized readily available starting materials, thereby avoiding the use of prefunctionalized starting materials, and was performed under metal‐free conditions thus, making it an alternate approach for the synthesis of furo[3,2‐ c ]coumarin derivatives. The reaction proceeds via a Michael addition/intra‐molecular cyclization/aromatization cascade to afford the desired product in moderate‐to‐good yields. As the compounds exhibit fluorescence under UV light, photophysical properties like absorption, emission of selected compounds, and solvatochromism were measured. Moreover, these compounds have potential pharmacological applications and can be employed as functional material, gram‐scale synthesis of desired fused‐heterocycles was demonstrated.

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Publication Details

Journal
Asian Journal of Organic Chemistry
Published
2025-05-22
DOI
https://doi.org/10.1002/ajoc.202500385
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Sulfur‐Promoted, DABCO‐Catalyzed Reaction of β‐Nitrostyrenes with 4‐Hydroxycoumarins: Access to Furo[3,2‐ c ]chromen‐4‐ones

C. Uma Maheswari, Karthiyayini Gnanaoli, Deepan Babu Rajkumar, Senthilmurugan Parameshwaran
Asian Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Sulfur‐Promoted, DABCO‐Catalyzed Reaction of β‐Nitrostyrenes with 4‐Hydroxycoumarins: Access to Furo[3,2‐ c ]chromen‐4‐ones

C. Uma Maheswari, Karthiyayini Gnanaoli, Deepan Babu Rajkumar, Senthilmurugan Parameshwaran
article en

Abstract

Abstract In this study, we report a simple and elegant method for the preparation of furo[3,2‐ c ]coumarins from the one‐pot, [3+2] annulations of β‐nitroalkenes with 4‐hydroxycoumarins in the presence of sulfur and DABCO as the catalyst. This method utilized readily available starting materials, thereby avoiding the use of prefunctionalized starting materials, and was performed under metal‐free conditions thus, making it an alternate approach for the synthesis of furo[3,2‐ c ]coumarin derivatives. The reaction proceeds via a Michael addition/intra‐molecular cyclization/aromatization cascade to afford the desired product in moderate‐to‐good yields. As the compounds exhibit fluorescence under UV light, photophysical properties like absorption, emission of selected compounds, and solvatochromism were measured. Moreover, these compounds have potential pharmacological applications and can be employed as functional material, gram‐scale synthesis of desired fused‐heterocycles was demonstrated.

Asian Journal of Organic ChemistryVol. 14(8)
SASTRA University (IN)
Openalex Percentile: Top 91%
Catalytic C–H Functionalization Methods
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