Abstract
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 N-nucleophile. Using iodoalkenes, the two nucleophiles were selectively converted to the corresponding amide in the presence of Pd(OAc)2/2 PPh3 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 N-acylnortropane derivatives of biological importance.
Highlights
Amide functionality can be found in numerous pharmaceutically, biologically active and agrochemical molecules [1,2,3], and its formation has been deeply studied [4,5]
The most efficient and widely-used method among the conventional amide synthesis is the reaction with acyl chlorides and amines [14,15,16,17,18]
Despite of the widespread use of acyl chlorides in amide synthesis, it has to be noted that acyl chlorides have significant limitations [6]
Summary
Amide functionality can be found in numerous pharmaceutically, biologically active and agrochemical molecules [1,2,3], and its formation has been deeply studied [4,5]. Activated carboxy compounds are widely used acylating agents producing the desired amide derivative in the presence of amines. The most efficient and widely-used method among the conventional amide synthesis is the reaction with acyl chlorides and amines [14,15,16,17,18]. Considering the fact that the palladium-catalyzed aminocarbonylation reactions have been widely applied to build-up amide functionality in several bioactive compounds and natural products, this method has been chosen to produce novel N-acylnortropane derivatives in our research. The high selectivity, the mild reaction conditions, and the tolerance of wide range of functional groups make more applicable the palladium-catalyzed aminocarbonylation for the synthesis of our target compounds than the conventional acylating methods. The selective synthesis of N-acylnortropane derivatives, possessing a variety of N-acyl moieties will be described
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
