NATURAL PRODUCTS AS TEMPLATES FOR BIOACTIVE COMPOUND LIBRARIES. 3. NOVEL HETEROCYCLES AND PEPTIDOMIMETICS GENERATED FROM ANABASINE BY ISOCYANIDE-BASED MULTICOMPONENT REACTIONS

Abstract

Anabasine served as a starting material for the synthesis of two series of novel, druglike compounds. On one hand, anabasine was subjected to a direct Chichibabin amination and elaborated into medicinally relevant, racemic 6-(piperidin-2-yl)imidazo[1,2-a]pyridines via the Groebke–Blackburn reaction. On the other hand, anabasin was used as an amine for the Ugi reaction to provide novel non-racemic anabasine-containing 2-[(2-pyridin-3-yl)piperidin-1-yl]acetamide peptidomimetics with high diastereoselectivity.

Also published in Chemistry of Heterocyclic Compounds, 2012, 48 (4), pp 606-612

http://link.springer.com/article/10.1007/s10593-012-1033-z