L-Ascorbic Acid: A Green and Competent Promoter for Solvent-Free Synthesis of Flavones and Coumarins under Conventional as well as Microwave Heating

Author(s): Rohit Arvind Dengale, Nitin Madhu Thorat, Shankar Ramchandra Thopate.

Journal Name: Letters in Organic Chemistry

Volume 13 , Issue 10 , 2016

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Abstract:

Background: An expeditious approach has been developed for the synthesis of two distinct classes of benzopyrones viz. flavones and coumarins under solvent-free conditions. L-Ascorbic acid was found to be an effective promoter under microwave irradiation and conventional heating. Various benzo-α-pyrones and benzo-γ-pyrones were synthesized with overall good yields. The present protocol is highly facile and needs no column chromatography for purification and therefore it would serve as an effective and compatible method under both microwave irradiation and conventional heating.

Results: The catalytic ability of L-ascorbic acid was investigated for the synthesis of flavones and coumarins. For this purpose, cyclodehydration of 1-(2-hydroxyphenyl)-3-aryl-1,3-propanedione and Pechmann coumarin synthesis, reactions were selected. And accordingly, it was observed that one mole of L-ascorbic acid was necessary for the completion of reaction. In all the cases, the desired flavones were smoothly generated with good to excellent yields; indicating its excellent tolerance for various functional groups. However, electron donating groups favors coumarin synthesis under these conditions. All the reaction mixtures were carefully analyzed and NMR indicates high conversions and lack of side products.

Conclusion: We have developed L-ascorbic acid-promoted, solvent-free and simple method for the synthesis of benzo-α-pyrones and benzo-γ-pyrone under microwave irradiation as well as conventional heating in good to excellent yields. The notable advantages of this method are solvent-free conditions, inexpensive and efficient eco-friendly promoter, and shorter reaction time and can be carried out under air. This methodology is highly facile and requires no column chromatography for purification. The resulting flavones and coumarins are versatile building blocks in the construction of heterocyclic architectures, dominant in natural products. Further studies of exploiting the efficiency of L-ascorbic acid as a promoter in synthesis of various heterocyclic compounds are in progress.

Keywords: L-Ascorbic acid, benzopyrone, flavone, coumarin, solvent-free synthesis, promoter.

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Article Details

VOLUME: 13
ISSUE: 10
Year: 2016
Page: [734 - 741]
Pages: 8
DOI: 10.2174/1570178614666161116125148
Price: $58

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