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

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

Volume: 14 Issue: 10

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

Affiliation:

• Ufa Institute of Chemistry of the Russian Academy of Sciences. Box: 71, pr. Oktyabrya, 450054, Ufa,Russian Federation

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

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.

Cite this article as:

Khusnutdinova F. Elmira *, Bremond Paul, Petrova V. Anastasiya , Kukovinets S. Olga and Kazakova B. Oxana , Synthesis of Lupane Mono- and Bis-C19-(1,2,3-triazolyl)-triterpenoids by “Click” Reaction, Letters in Organic Chemistry 2017; 14 (10) . https://dx.doi.org/10.2174/1570178614666170918120624