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

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

Журнал

Reaction Kinetics, Mechanisms and Catalysis
ISSN: 1878-5190 , E-ISSN: 1878-5204

Вых. Данные

Год: 2020, Том: 129, Номер: 2, Страницы: 627-644 Страниц : 18 DOI: 10.1007/s11144-020-01740-9

Ключевые слова

Chromenol; Sulfonated clay; Isopulegol; Ketones

Авторы

Laluc Mathias ¹ , Maki-Arvela Paivi ¹ , Peixoto Andreia F. ² , Li-Zhulanov Nikolai ^3,4 , Sandberg Thomas ¹ , Salakhutdinov Nariman F. ³ , Volcho Konstantin ^3,4 , Freire Cristina ² , Sidorenko Alexander Yu ⁵ , Murzin Dmitry Yu ¹

Организации

1	(Данные Web of science) Abo Akad Univ, Turku 20500, Finland
2	(Данные Web of science) Univ Porto, LAQV REQUIMTE, Fac Ciencias, Dept Quim E Bioquim, Rua Campo Alegre S-N, P-4169007 Porto, Portugal
3	(Данные Web of science) Novosibirsk Inst Organ Chem, Lavrentjev Av 9, Novosibirsk 630090, Russia
4	(Данные Web of science) Novosibirsk State Univ, Pirogova St 1, Novosibirsk 630090, Russia
5	(Данные Web of science) Natl Acad Sci Belarus, Inst Chem New Mat, Skaryna Str 36, Minsk 220141, BELARUS

Condensation of (-)-isopulegol with acetone was investigated at 25-40 degrees 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 degrees C. The yield exceeded that of other previously reported in the open literature catalysts.

Laluc M. , Maki-Arvela P. , Peixoto A.F. , Li-Zhulanov N. , Sandberg T. , Salakhutdinov N.F. , Volcho K. , Freire C. , Sidorenko A.Y. , Murzin D.Y.
Catalytic synthesis of bioactive 2H-chromene alcohols from (-)-isopulegol and acetone on sulfonated clays

Reaction Kinetics, Mechanisms and Catalysis. 2020. V.129. N2. P.627-644. DOI: 10.1007/s11144-020-01740-9 WOS Scopus РИНЦ

Полный текст от издателя

Опубликована online:	20 февр. 2020 г.
Опубликована в печати:	1 апр. 2020 г.

Web of science	WOS:000516301700001
Scopus	2-s2.0-85079669741
РИНЦ	43248272
OpenAlex	W3007301671