Selective Synthesis of N-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation

László Kollár; Ádám Erdélyi; Haroon Rasheed; Attila Takács

doi:10.3390/molecules26061813

Selective Synthesis of N-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation

Molecules. 2021 Mar 23;26(6):1813. doi: 10.3390/molecules26061813.

Authors

László Kollár^{1

2

3}, Ádám Erdélyi¹, Haroon Rasheed¹, Attila Takács^{1

2}

Affiliations

¹ Department of Inorganic Chemistry, Faculty of Sciences, University of Pécs, Ifjúság útja 6, H-7624 Pécs, Hungary.
² János Szentágothai Research Centre, University of Pécs, Ifjúság útja 20, H-7624 Pécs, Hungary.
³ MTA-PTE Research Group for Selective Chemical Syntheses, Ifjúság útja 6, H-7624 Pécs, Hungary.

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.

Keywords: N-acylnortropanes; aminocarbonylation; carbon monoxide; palladium.

MeSH terms

Catalysis
Molecular Structure
Nortropanes / chemical synthesis*
Nortropanes / chemistry*
Palladium / chemistry*

Substances

Nortropanes
Palladium

Abstract

MeSH terms

Substances

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