Cs<sub>2</sub>CO<sub>3</sub>‐I<sub>2</sub> Promoted Efficient Synthesis of Flavones and Flavanones: Total Synthesis of Narengenin and Apigenin

Abstract Flavonoids are an important class of naturally existing scaffolds known for their diverse biological activities and have been immensely synthesized using stoichiometric reagent amounts. Herein, we report a reliable, robust, one‐pot, transition metal and additive‐free protocol for the synthesis of flavones and flavanones from 2‐hydroxyacetophenone and substituted aldehydes. Our developed method utilizes Cs 2 CO 3 as a base and iodine as an oxidant in H 2 O: DMSO (9 : 1) solvent system, which provides direct access to many flavones and flavanones in excellent yields under milder reaction conditions with simple yet easily available substrates. In application, naturally occurring compounds such as naringenin and apigenin have been successfully synthesized using developed protocol.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2024-12-28
DOI
https://doi.org/10.1002/ejoc.202401298
Primary Topic
Bioactive natural compounds
Type
article
Field-Weighted Citation Impact
0.00

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article

Cs2CO3‐I2 Promoted Efficient Synthesis of Flavones and Flavanones: Total Synthesis of Narengenin and Apigenin

Rohan D. Erande, Kailas Arjun Chavan
European Journal of Organic Chemistry
Bioactive natural compounds
article

Cs2CO3‐I2 Promoted Efficient Synthesis of Flavones and Flavanones: Total Synthesis of Narengenin and Apigenin

Rohan D. Erande, Kailas Arjun Chavan
article en

Abstract

Abstract Flavonoids are an important class of naturally existing scaffolds known for their diverse biological activities and have been immensely synthesized using stoichiometric reagent amounts. Herein, we report a reliable, robust, one‐pot, transition metal and additive‐free protocol for the synthesis of flavones and flavanones from 2‐hydroxyacetophenone and substituted aldehydes. Our developed method utilizes Cs 2 CO 3 as a base and iodine as an oxidant in H 2 O: DMSO (9 : 1) solvent system, which provides direct access to many flavones and flavanones in excellent yields under milder reaction conditions with simple yet easily available substrates. In application, naturally occurring compounds such as naringenin and apigenin have been successfully synthesized using developed protocol.

European Journal of Organic ChemistryVol. 28(9)
Indian Institute of Technology Jodhpur (IN)
Indian Institute of Technology Jodhpur, Ministry of AYUSH, Government of India, Department of Science and Technology, Ministry of Science and Technology, India, Ministry of Education, India, Ministry of Ayurveda, Yoga and Naturopathy, Unani, Siddha and Homoeopathy
Openalex Percentile: Top 79%
Bioactive natural compounds
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Cs<sub>2</sub>CO<sub>3</sub>‐I<sub>2</sub> Promoted Efficient Synthesis of Flavones and Flavanones: Total Synthesis of Narengenin and Apigenin — Rohan D. Erande, Kailas Arjun Chavan · European Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS