Catalytic synthesis of bioactive 2H-chromene alcohols from (−)-isopulegol and acetone on sulfonated clays

Mathias Laluc, Päivi Mäki-Arvela, Andreia F. Peixoto, Nikolai Li-Zhulanov, Thomas Sandberg, Nariman F. Salakhutdinov, Konstantin Volcho, Cristina Freire, Alexander Yu Sidorenko, Dmitry Yu Murzin

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Condensation of (−)-isopulegol with acetone was investigated at 25–40 °C over clay based materials (K10, cloisite Na+ and halloysite nanotubes) modified with sulfonic acid groups by one-pot sulfonation with chlorosulfonic acid or via organosilylation with 2-(4-chlrosulfonylphenyl)-ethyltrimethoxysilane. The target product was the R diastereomer of dimethyl-substituted octahydro-2H-chromen-4-ol with exhibits antiviral activity. The catalysts were characterized by a range of physico-chemical methods. The effect of the initial isopulegol concentrations on the yield of ketone-derived chromenols and the R/S isomers ratio was studied for the first time. The best catalyst was a highly acidic, large pore K10-clay modified by sulfonic acid. Varying the initial concentration of the reagents allows to find a balance between dehydration by-products and a side etherification reaction. A high yield (73%) of the desired chromenols was reached using 0.52 mol/l initial (−)-isopulegol concentration after 240 min at 87% substrate conversion and reaction temperature 25 °C. The yield exceeded that of other previously reported in the open literature catalysts.

Original languageEnglish
Pages (from-to)627-644
Number of pages18
JournalReaction Kinetics, Mechanisms and Catalysis
Volume129
Issue number2
DOIs
Publication statusPublished - 1 Apr 2020

Keywords

  • Chromenol
  • Isopulegol
  • Ketones
  • Sulfonated clay
  • OCTAHYDRO-2H-CHROMEN-4-OL
  • ESTERIFICATION
  • ISOPULEGOL
  • MODEL
  • ANALGESIC ACTIVITY
  • PRINS CYCLIZATION
  • VANILLIN
  • MODIFIED HALLOYSITE NANOTUBES
  • ACIDITY

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