| Abstract [eng] |
Synthesis of asymmetric naphthalene diimide, that contains pyrrolidinylmethylamine fragment, was performed in this work on purpose to investigate its catalitic properties for enamine actyvation. Firstly, pyrrolidin-2-ylmethaneamine was synthesised using L-proline as a starting material. Two different synthesis pathways were tried for this procedure. One of them contained reduction of carboxylic acid, protection of amine by Boc protecting group, mesylation of alcohol, substitution of mesyl fragment and reduction of azide. Another one was performed by using benzylation, esterification, substitution and reduction reactions. In parallel with pyrrolidin-2-ylmethaneamine synthesis, naphthalene monoimide (13, 14, 15) was synthesized as well. Few different methods were used in order to optimize this procedure. It was observed that initial sonification or reflux of starting mixture is crucial for quantitative synthesis of monoimide. Condensation reactions of intermediates led to the formation of NDI derivatives with incorporated benzyl (5, 6) or Boc (12, 16) fragments. Further, removal of these protecting groups was carried out. All attempts to remove benzyl fragment were unsuccessful in this step. Deprotection of Boc-amine 16 gave desired asymmetric NDI 17. Finaly, few enamine actyvation reactions were tried with various aldehydes and ketones using NDI 17 as a model catalyst. At this point, it was observed that ketone group is unreactive in tested catalytic system meanwhile use of aldehydes lead to the formation of desired enamine structure. |
