A Novel Heterocyclic System Based on Natural Epoxyalantolactone

Natural sesquiterpene lactones which contain an exocyclic methylene group in the β-position of the lactone ring react readily with N-nucleophiles. When studying the reaction of the natural epoxyalantolactone with the primary amines we demonstrate the formation of a new heterocyclic system—the hydrog...

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Published inFrontiers in chemistry Vol. 7; p. 655
Main Authors Klochkov, Sergey G., Pukhov, Sergey A., Afanasieva, Svetlana V., Neganova, Margarita E., Ananiev, Ivan V., Avila-Rodriguez, Marco, Tarasov, Vadim V., Aliev, Gjumrakch
Format Journal Article
LanguageEnglish
Published Frontiers Media S.A 01.10.2019
Subjects
Chemistry
epoxyalantolactone
Michael reaction
new heterocyclic system
sesquiterpene lactones
synthesis
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Summary:Natural sesquiterpene lactones which contain an exocyclic methylene group in the β-position of the lactone ring react readily with N-nucleophiles. When studying the reaction of the natural epoxyalantolactone with the primary amines we demonstrate the formation of a new heterocyclic system—the hydrogenated benzo[g]furo[4,3,2-cd]indol-3(1H)-one. Spectral data on the characteristics of the synthesized compounds are presented. The data on the reaction mechanisms and its applicability for the preparation are discussed.
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Edited by: Laurent G. Désaubry, Laboratoire de Cardio-Oncologie et Chimie Médicinale (CNRS), France
Reviewed by: Andrei I. Khlebnikov, Tomsk Polytechnic University, Russia; Michele Mari, University of Urbino Carlo Bo, Italy
This article was submitted to Medicinal and Pharmaceutical Chemistry, a section of the journal Frontiers in Chemistry
ISSN:2296-2646
2296-2646
DOI:10.3389/fchem.2019.00655