Convenient One-Pot Synthesis of Chromone Derivatives and Their Antifungal and Antibacterial Evaluation

Abstract

A one-pot method for the synthesis of chromone derivatives from the reaction of 2-hydroxyacetophenones with aliphatic or aromatic acid chlorides is reported. Esterification and Baker–Venkataraman rearrangement were promoted by t-BuOK, which was followed directly by acid-catalyzed cyclization in one pot. Some of 2-cyclohexyl- and 2-cyclohexylmethyl-substituted chromones displayed activity against plant pathogenic fungal strains.

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GRAPHICAL ABSTRACT

Keywords:

• Antifungal activity
• chromones
• flavonoids
• heterocycles

ACKNOWLEDGMENT

This work was partially supported by the Egyptian Ministry of Higher Education and State for Scientific Research (MHESR) under the ParOwn programe.

Notes

^a Indicates isolated yield of analytically pure material.

^a Indicates isolated yield of analytically pure material.

^b Isolated yield obtained under modified conditions for the cyclisation step (0.2 M H₂SO₄).

^a IC₅₀ values are reported in µg/cm².

^b Compounds 5ec, 5ef, and 5eg did not display activity in the assays up to 42 µg/cm².