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Copper-catalyzed 1,3-dipolar cycloaddition reaction of spirosolanederived azide for the preparation of modified solasodine alkaloid Full article

Journal Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353
Output data Year: 2018, Volume: 54, Number: 4, Pages: 411-416 Pages count : 6 DOI: 10.1007/s10593-018-2284-0
Tags solasodine; steroidal alkaloids; 1,2,3-triazoles; azidolysis; CuAAC reaction
Authors Finke Anastasiya O. 1,2 , Mironov Maxim E. 1,2 , Skorova Anna B. 1 , Shults Elvira E. 1,2
Affiliations
1 (Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, 9 Akad Lavrentieva Ave, Novosibirsk 630090, Russia
2 (Данные Web of science) Novosibirsk State Univ, 1 Pirogova St, Novosibirsk 630090, Russia

Abstract: Modification of the steroidal alkaloid solasodine was performed by introduction of 1,2,3-triazolyl substituents at the D-6 atom of spirosolane ring system. The azidolysis of 5,6 alpha-epoxysolasodine diacetate, formed as the major product during epoxidation of solasodine diacetate by the action of sodium azide in DMF in the presence of ammonium chloride, proceeded through the formation of 6 beta-azido-5 alpha-hydroxysolasodine diacetate. The newly obtained azide was used in reactions with terminal alkynes in the presence of copper(I) bromide and N,N-diisopropylethylamine in DMF to synthesize the respective (22R,25R)-N,O-diacetyl-6 beta-[4-aryl-1,2,3-triazol-1-yl]-5 alpha-hydroxyspirosolanes.
Cite: Finke A.O. , Mironov M.E. , Skorova A.B. , Shults E.E.
Copper-catalyzed 1,3-dipolar cycloaddition reaction of spirosolanederived azide for the preparation of modified solasodine alkaloid
Chemistry of Heterocyclic Compounds. 2018. V.54. N4. P.411-416. DOI: 10.1007/s10593-018-2284-0 WOS Scopus РИНЦ
Dates:
Published print: Apr 1, 2018
Published online: Jun 8, 2018
Identifiers:
Web of science WOS:000435354700008
Scopus 2-s2.0-85048264965
Elibrary 35754210
OpenAlex W2806629566
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