Synthesis of 4-Aryldihydrocoumarins via a Sequential Michael Addition–Lactonization Route

(E-pub Abstract Ahead of Print)

Author(s): Anshu Kumar Sinha, Chandra Mohan Srivastava, Gyandshwar K. Rao, Manvika Karnatak, Ved Prakash Verma*, Varun Rawat*

Journal Name: Current Organocatalysis

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Background: Coumarin and its derivatives have attracted the attention of synthetic chemists due to their importance in pharmaceutical and medicinal chemistry. The acid-catalyzed cyclization route constitutes the method of choice to access these important compounds.

Objective: In this paper, we have discussed the synthesis of 4-aryldihydrocoumarins via a one-pot p-sulfonic acid calix[4]arene catalyzed reaction.

Method: The easily prepared calix[4]arene derivative catalyzes a sequential reaction involving Michael addition followed by intramolecular lactonization to afford the title compound in decent yield.

Results: The described methodology is devoid of any metal salt, thus making it a very appealing protocol to safely produce dihydrocoumarins of pharmacological importance.

Conclusion: The easy recovery, non-toxicity, and reusability of the catalytic system are some of the other advantages of our procedure. In addition, the catalyst efficiency is not compromised after its successive use in reactions.

Keywords: Organocatalysis, Calixarene, Sequential reactions, Coumarins, Michael addition, Lactonization

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Article Details

(E-pub Abstract Ahead of Print)
DOI: 10.2174/2213337208666210223151108
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