Baker-Venkataraman Rearrangement Under Microwave Irradiation: A New Strategy for the Synthesis of 3-Aroyl-5-hydroxyflavones

Chromones (4H‐chromen‐4‐ones) contemplate a naturally occurring class of compounds widely distributed in Nature, particularly in plants. This singular ring system has emerged as a privileged scaffold in medicinal chemistry, mainly due to its unique structural features, diverse biological activities, and pharmacological properties. Throughout the past few years, our efforts have been focused on synthesizing a series of 2‐benzylchromones through a Claisen condensation, using 2’‐hydroxyacetophenones and ethyl 2‐phenylacetates. However, the extended periods of reaction necessary for the synthesis of 2‐benzylchromones led to the search for an alternative. Thus, microwave irradiation emerged as a suitable approach to obtain these chromones in shorter reaction times and with similar or even improved synthetic yields. Our work demonstrates that it is possible to synthesize 2‐benzylchromones through both conventional and microwave‐assisted synthesis, favoring the use of microwave irradiation.

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A Valuable Method for the Synthesis of 2‐Benzylchromones: A Comparative Evaluation of Both Conventional and Microwave‐Assisted Synthesis

Silva

Pacheco

Pinto

et al. 2022

ChemistrySelect

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Choline hydroxide, an efficient, green, and recyclable base catalyst, promoted the synthesis of 3-aroylflavones via Baker–Venkataraman rearrangement

Nguyen,

Vo,

Bui

et al. 2024

Green Chemistry Letters and Reviews

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One-Pot Green Synthesis of 2-Hydroxybenzoyl(cinnamoyl)methanes and 2-Styrylchromones Using Dual-Frequency Ultrasonication

et al. 2020

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Baker-Venkataraman Rearrangement Under Microwave Irradiation: A New Strategy for the Synthesis of 3-Aroyl-5-hydroxyflavones

Abstract: Microwave irradiation selectively induces the Baker-Venkataraman rearrangement of 2¢,6¢-diaroyloxyacetophenones to give 3-aroyl-5-hydroxyflavones, in a very short reaction time. Under classical heating conditions these reactions afforded 5-hydroxyflavones as byproducts.

Cited by 5 publications

References 5 publications

A Valuable Method for the Synthesis of 2‐Benzylchromones: A Comparative Evaluation of Both Conventional and Microwave‐Assisted Synthesis

A Valuable Method for the Synthesis of 2‐Benzylchromones: A Comparative Evaluation of Both Conventional and Microwave‐Assisted Synthesis

Choline hydroxide, an efficient, green, and recyclable base catalyst, promoted the synthesis of 3-aroylflavones via Baker–Venkataraman rearrangement

One-Pot Green Synthesis of 2-Hydroxybenzoyl(cinnamoyl)methanes and 2-Styrylchromones Using Dual-Frequency Ultrasonication

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