Copper-catalyzed 1,3-dipolar cycloaddition reaction of spirosolanederived azide for the preparation of modified solasodine alkaloid Full article
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Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353 |
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| 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 | ||||
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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 OpenAlex
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 OpenAlex
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 |