Department of Inorganic Chemistry, Faculty of Sciences, University of Pécs, Ifjúság útja 6, H-7624 Pécs, Hungary.
János Szentágothai Research Centre, University of Pécs, Ifjúság útja 20, H-7624 Pécs, Hungary.
Molecules. 2021 Mar 23;26(6):1813. doi: 10.3390/molecules26061813.
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 -nucleophile. Using iodoalkenes, the two nucleophiles were selectively converted to the corresponding amide in the presence of Pd(OAc)/2 PPh 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 -acylnortropane derivatives of biological importance.
采用具有生物重要性的托烷类胺，如 8-氮杂双环[3.2.1]辛-3-酮（降诺托品）和 3α-羟基-8-氮杂双环[3.2.1]辛烷（降诺品）作为亲核试剂，进行了各种烯基和（杂）芳基碘化物的氨甲酰化反应。在 Pd(OAc)/2 PPh 催化剂存在下，两种亲核试剂可选择性地将碘代烯烃转化为相应的酰胺。在几种碘代（杂）芳基存在下，需要使用双齿 Xantphos 来选择性地生成目标化合物。通过钯催化的氨甲酰化反应形成的各种结构的新的羧酰胺被分离并进行了完全表征。通过这种方式，开发了一种用于合成具有生物重要性的-酰基降诺托烷衍生物的新的合成方法。
