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

Imani M., Pesyan N. N., Aalinejad M., ŞAHİN E.

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, cilt.19, sa.8, ss.3397-3405, 2022 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 19 Sayı: 8
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1007/s13738-022-02533-8
  • Dergi Adı: JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Sayfa Sayıları: ss.3397-3405
  • Anahtar Kelimeler: 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
  • Atatürk Üniversitesi Adresli: Evet

Özet

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.