Synthesis and Properties of (+)-Ketopinic and (–)-Camphanic Acids Esters Bearing a Nitrogen-Containing Heterocycle

Synthesis and Properties of (+)-Ketopinic and (–)-Camphanic Acids Esters Bearing a Nitrogen-Containing Heterocycle Full article

Journal

Russian Journal of General Chemistry
ISSN: 1070-3632 , E-ISSN: 1608-3350

Output data

Year: 2023, Volume: 93, Number: 12, Pages: 3062-3073 Pages count : 12 DOI: 10.1134/s1070363223120058

Authors

Sokolova A.S. ¹ , Yarovaya O.I. ¹ , Kuzminykh L.V. ¹ , Ilyina M.G. ² , Borisevich S.S. ² , Esaulkova Ya.L. ³ , Zarubaev V.V. ³ , Salakhutdinov N.F. ¹

Affiliations

1	N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences
2	Ufa Institute of Chemistry, RAS
3	Saint Petersburg Pasteur Institute

Funding (1)

Российский Научный Фонд

22-23-00618

A three-stage method was proposed for the synthesis of (1S)-(+)-camphor-10-sulfonic acid, (+)-ketopinic and (–)-camphanic acids esters containing a saturated nitrogen-containing heterocycle. It was found that (1S)-(+)-camphor-10-sulfonic acid esters undergo destruction with elimination of the sulfonic acid group in substitution reactions involving nitrogen-containing heterocycles. Esters of (+)-ketopinic and (–)-camphanic acids were formed during the proposed synthetic route, but undergo transesterification under column chromatography conditions. Quantum chemical calculations showed that the destruction of the ester bond in the case of (+)-ketopinic and (–)-camphanic acids requires less energy than the breaking of a similar bond in (–)-borneol esters. It was revealed that the internal bond strength index (IBSI) for the alkyl C–O bond in (–)-borneol esters is higher than in (+)-ketopinic and (–)-camphanic acid esters. Antiviral properties against the H1N1 influenza virus were studied for derivatives of (+)-ketopinic and (–)-camphanic acids.

Sokolova A.S. , Yarovaya O.I. , Kuzminykh L.V. , Ilyina M.G. , Borisevich S.S. , Esaulkova Y.L. , Zarubaev V.V. , Salakhutdinov N.F.
Synthesis and Properties of (+)-Ketopinic and (–)-Camphanic Acids Esters Bearing a Nitrogen-Containing Heterocycle
Russian Journal of General Chemistry. 2023. V.93. N12. P.3062-3073. DOI: 10.1134/s1070363223120058 WOS Scopus РИНЦ OpenAlex

Соколова А.С. , Яровая О.И. , Кузьминых Л.В. , Ильина М.Г. , Борисевич С.С. , Есаулкова Я.Л. , Зарубаев В.В. , Салахутдинов Н.Ф.
Синтез и свойства сложных эфиров (+)-кетопиновой и (-)-камфановой кислот, включающих азотсодержащий гетероцикл
Журнал общей химии (RUSS J GEN CHEM+). 2023. Т.93. №12. С.1854-1866. DOI: 10.31857/S0044460X23120053 РИНЦ OpenAlex

Submitted:	Nov 12, 2023
Accepted:	Nov 15, 2023
Published online:	Jan 26, 2024

Web of science:	WOS:001151114800014
Scopus:	2-s2.0-85183407609
Elibrary:	64552454
OpenAlex:	W4391266037

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