Research output: Contribution to journal › Article › peer-review
Catalytic synthesis of bioactive 2H-chromene alcohols from (−)-isopulegol and acetone on sulfonated clays. / Laluc, Mathias; Mäki-Arvela, Päivi; Peixoto, Andreia F. et al.
In: Reaction Kinetics, Mechanisms and Catalysis, Vol. 129, No. 2, 01.04.2020, p. 627-644.Research output: Contribution to journal › Article › peer-review
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TY - JOUR
T1 - Catalytic synthesis of bioactive 2H-chromene alcohols from (−)-isopulegol and acetone on sulfonated clays
AU - Laluc, Mathias
AU - Mäki-Arvela, Päivi
AU - Peixoto, Andreia F.
AU - Li-Zhulanov, Nikolai
AU - Sandberg, Thomas
AU - Salakhutdinov, Nariman F.
AU - Volcho, Konstantin
AU - Freire, Cristina
AU - Sidorenko, Alexander Yu
AU - Murzin, Dmitry Yu
N1 - Publisher Copyright: © 2020, The Author(s). Copyright: Copyright 2020 Elsevier B.V., All rights reserved.
PY - 2020/4/1
Y1 - 2020/4/1
N2 - 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.
AB - 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.
KW - Chromenol
KW - Isopulegol
KW - Ketones
KW - Sulfonated clay
KW - OCTAHYDRO-2H-CHROMEN-4-OL
KW - ESTERIFICATION
KW - ISOPULEGOL
KW - MODEL
KW - ANALGESIC ACTIVITY
KW - PRINS CYCLIZATION
KW - VANILLIN
KW - MODIFIED HALLOYSITE NANOTUBES
KW - ACIDITY
UR - http://www.scopus.com/inward/record.url?scp=85079669741&partnerID=8YFLogxK
U2 - 10.1007/s11144-020-01740-9
DO - 10.1007/s11144-020-01740-9
M3 - Article
AN - SCOPUS:85079669741
VL - 129
SP - 627
EP - 644
JO - Reaction Kinetics, Mechanisms and Catalysis
JF - Reaction Kinetics, Mechanisms and Catalysis
SN - 1878-5190
IS - 2
ER -
ID: 23583106