Selective Synthesis of <i>N</i>-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation

The aminocarbonylation of various alkenyl and (hetero)aryl iodides was carried out using tropane-based amines of biological importance, such as 8-azabicyclo[3.2.1]octan-3-one (nortropinone) and 3α-hydroxy-8-azabicyclo[3.2.1]octane (nortropine) as <i>N</i>-nucleophile. Using iodoalkenes,...

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Bibliographic Details
Main Authors: László Kollár, Ádám Erdélyi, Haroon Rasheed, Attila Takács
Format: Article
Language:English
Published: MDPI AG 2021-03-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/26/6/1813
Description
Summary:The aminocarbonylation of various alkenyl and (hetero)aryl iodides was carried out using tropane-based amines of biological importance, such as 8-azabicyclo[3.2.1]octan-3-one (nortropinone) and 3α-hydroxy-8-azabicyclo[3.2.1]octane (nortropine) as <i>N</i>-nucleophile. Using iodoalkenes, the two nucleophiles were selectively converted to the corresponding amide in the presence of Pd(OAc)<sub>2</sub>/2 PPh<sub>3</sub> catalysts. In the presence of several iodo(hetero)arenes, the application of the bidentate Xantphos was necessary to produce the target compounds selectively. The new carboxamides of varied structure, formed in palladium-catalyzed aminocarbonylation reactions, were isolated and fully characterized. In this way, a novel synthetic method has been developed for the producing of <i>N</i>-acylnortropane derivatives of biological importance.
ISSN:1420-3049