Article 2022 · 3 citations

Study of chemical behaviors of 4-hydroxycumarin in alkali media: dicumarols or dihydro-4<i>H</i>-furo[3,2-<i>c</i>]chromenes?

Imani, Masoumeh, Pesyan, Nader Noroozi, Aalinejad, Michael, Sahin, Ertan

Abstract

A novel method for one-pot reaction of 4-hydroxycoumarin with various aldehydes and trimethylamine (Et3N) leads to dicumarols and quaternary dicumarol-triethylammonium salts in the presence of cyanogen bromide (BrCN). The same reactions were proceeded in the presence of sodium ethoxide (EtONa) that leads to dicumarols in good to excellent yields at room temperature. Exceptionally, 4-hydroxybenzaldehyde in the reaction with 4-hydroxycoumarin and BrCN in the presence of EtONa led to selective and efficacious formation of dihydro-4H-furo [3,2-c] chromene derivative, under the same condition. All structures elucidation was characterized by H-1, C-13 NMR, FT-IR spectroscopy. Furocumarin derivative was also specified by X-ray crystallography technique.

Keywords

4-Hydroxycoumarin Dihydro-4H-furo [3 2-c] chromene Dicumarol Aldehyde One-pot reaction Cyanogen bromide Transesterification Centrosymmetric twenty-membered ring ANTIMICROBIAL ACTIVITY COUMARIN DERIVATIVES DICOUMAROL ANTIBACTERIAL COMPLEXES

WoS Categories

Chemistry, Multidisciplinary

Sustainable Development Goals

Good Health and Well-being

Citation

Journal: JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
Year: 2022
Volume: 19
Issue: 8
Pages: 3397-3405
ISSN: 1735-207X
eISSN: 1735-2428
DOI: 10.1007/s13738-022-02533-8
WoS UID: WOS:000776061600001

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