Synthesis of Lupane Mono- and Bis-C19-(1,2,3-triazolyl)-triterpenoids by “Click” Reaction

Author(s): Elmira F. Khusnutdinova* , Paul Bremond , Anastasiya V. Petrova , Olga S. Kukovinets , Oxana B. Kazakova .

Journal Name: Letters in Organic Chemistry

Volume 14 , Issue 10 , 2017

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Abstract:

A series of lupane C19-(1,2,3-triazolyl)-triterpenoids were obtained by “click” reaction of 3,28-diacetoxy-29-norlup- 20(30)-yne with different aromatic and sugar azides after screening of several copper-based catalytic systems. DFT calculations were performed (B3LYP/6.311 level of theory) and showed that the alkyne moiety is hindered by the triterpenoid skeleton, thus explaining its low reactivity and the requirement of a very active catalytic system. Ultimately, it was found that the dinuclear copper complex [Cu(µ-OH)(TMEDA)]2Cl2 is the most efficient catalyst. Moreover, for the first time, a bis-(triazolyltriterpenoid)-derivative was obtained by the reaction of lupane C19-alkyne with 1,4-bis(azidomethyl)benzene using the same catalyst.

Keywords: Triterpenoids, betulin, lupanes, 1, 2, 3-triazoletriterpenes, “click” reaction, C19-(1, 2, 3-triazolyl)-lupanes.

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Article Details

VOLUME: 14
ISSUE: 10
Year: 2017
Page: [743 - 747]
Pages: 5
DOI: 10.2174/1570178614666170918120624
Price: $58

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