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Copper-catalyzed 1,3-dipolar cycloaddition reaction of spirosolanederived azide for the preparation of modified solasodine alkaloid. / Finke, Anastasiya O.; Mironov, Maxim E.; Skorova, Anna B. et al.

In: Chemistry of Heterocyclic Compounds, Vol. 54, No. 4, 04.2018, p. 411-416.

Research output: Contribution to journal › Article › peer-review

Harvard

Finke, AO, Mironov, ME, Skorova, AB & Shults, EE 2018, 'Copper-catalyzed 1,3-dipolar cycloaddition reaction of spirosolanederived azide for the preparation of modified solasodine alkaloid', Chemistry of Heterocyclic Compounds, vol. 54, no. 4, pp. 411-416. https://doi.org/10.1007/s10593-018-2284-0

APA

Finke, A. O., Mironov, M. E., Skorova, A. B., & Shults, E. E. (2018). Copper-catalyzed 1,3-dipolar cycloaddition reaction of spirosolanederived azide for the preparation of modified solasodine alkaloid. Chemistry of Heterocyclic Compounds, 54(4), 411-416. https://doi.org/10.1007/s10593-018-2284-0

Vancouver

Finke AO, Mironov ME, Skorova AB, Shults EE. Copper-catalyzed 1,3-dipolar cycloaddition reaction of spirosolanederived azide for the preparation of modified solasodine alkaloid. Chemistry of Heterocyclic Compounds. 2018 Apr;54(4):411-416. doi: 10.1007/s10593-018-2284-0

Author

Finke, Anastasiya O. ; Mironov, Maxim E. ; Skorova, Anna B. et al. / Copper-catalyzed 1,3-dipolar cycloaddition reaction of spirosolanederived azide for the preparation of modified solasodine alkaloid. In: Chemistry of Heterocyclic Compounds. 2018 ; Vol. 54, No. 4. pp. 411-416.

BibTeX

@article{26b9334186584c158f81277136734a03,
title = "Copper-catalyzed 1,3-dipolar cycloaddition reaction of spirosolanederived azide for the preparation of modified solasodine alkaloid",
abstract = "Modification of the steroidal alkaloid solasodine was performed by introduction of 1,2,3-triazolyl substituents at the С-6 atom of spirosolane ring system. The azidolysis of 5,6α-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 6β-azido-5α-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-6β-[4-aryl-1,2,3-triazol-1-yl]-5α-hydroxyspirosolanes.",
keywords = "1,2,3-triazoles, azidolysis, CuААС reaction, solasodine, steroidal alkaloids, CANCER-CELLS, SOLANUM-TRILOBATUM, ANALOGS, INCANUM, IN-VITRO, CuAAC reaction, 1,2,3-TRIAZOLES, DERIVATIVES, TRANSFORMATIONS, CONSTITUENTS",
author = "Finke, {Anastasiya O.} and Mironov, {Maxim E.} and Skorova, {Anna B.} and Shults, {Elvira E.}",
year = "2018",
month = apr,
doi = "10.1007/s10593-018-2284-0",
language = "English",
volume = "54",
pages = "411--416",
journal = "Chemistry of Heterocyclic Compounds",
issn = "0009-3122",
publisher = "Springer New York",
number = "4",

}

RIS

TY - JOUR

T1 - Copper-catalyzed 1,3-dipolar cycloaddition reaction of spirosolanederived azide for the preparation of modified solasodine alkaloid

AU - Finke, Anastasiya O.

AU - Mironov, Maxim E.

AU - Skorova, Anna B.

AU - Shults, Elvira E.

PY - 2018/4

Y1 - 2018/4

N2 - Modification of the steroidal alkaloid solasodine was performed by introduction of 1,2,3-triazolyl substituents at the С-6 atom of spirosolane ring system. The azidolysis of 5,6α-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 6β-azido-5α-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-6β-[4-aryl-1,2,3-triazol-1-yl]-5α-hydroxyspirosolanes.

AB - Modification of the steroidal alkaloid solasodine was performed by introduction of 1,2,3-triazolyl substituents at the С-6 atom of spirosolane ring system. The azidolysis of 5,6α-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 6β-azido-5α-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-6β-[4-aryl-1,2,3-triazol-1-yl]-5α-hydroxyspirosolanes.

KW - 1,2,3-triazoles

KW - azidolysis

KW - CuААС reaction

KW - solasodine

KW - steroidal alkaloids

KW - CANCER-CELLS

KW - SOLANUM-TRILOBATUM

KW - ANALOGS

KW - INCANUM

KW - IN-VITRO

KW - CuAAC reaction

KW - 1,2,3-TRIAZOLES

KW - DERIVATIVES

KW - TRANSFORMATIONS

KW - CONSTITUENTS

UR - http://www.scopus.com/inward/record.url?scp=85048264965&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/e7ce8d3d-6a38-3d43-af4d-fef771d28ee7/

U2 - 10.1007/s10593-018-2284-0

DO - 10.1007/s10593-018-2284-0

M3 - Article

AN - SCOPUS:85048264965

VL - 54

SP - 411

EP - 416

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 4

ER -

ID: 13924911