Priprava izbranih 2-naftilaminov z Buchererjevo reakcijo

Rupnik, Nika (author), Košmrlj, Janez (mentor)

V diplomskem delu je predstavljena sinteza treh 2-naftilaminskih produktov. Sintezo smo izvajali v dveh stopnjah. V prvi smo uspešno pripravili ketonski derivat iz 6-bromo-2-naftola in 2-hidroksietil vinil etra s Heckovo reakcijo. Pri reakciji je kot katalizator nastopal in situ tvorjen paladijev(0) kompleks. V drugi stopnji smo hidroksilno skupino 1-(6-hidroksinaftalen-2-il)etan-1-ona zamenjali z izbranim sekundarnim aminom (dimetilaminom, piperidinom ali pirolidinom). Reakcija, ki smo jo izvajali v avtoklavu, je potekala po mehanizmu Buchererjeve reakcije. Sinteze vseh treh produktov so bile uspešno izvedene, produkti pa ustrezno okarakterizirani.

• Language: Slovenian
• Keywords: Buchererjeva reakcija, Heckova reakcija, 2-naftilamini, paladijev katalizator
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2023
• PID: 20.500.12556/RUL-149229
• COBISS.SI-ID: 167193603
• Publication date in RUL: 05.09.2023

Secondary language

• Language: English
• Title: Preparation of selected 2-naphthylamines by Bucherer reaction

Abstract

This bachelor's thesis presents the synthesis of three distinct 2-naphthylamines through a two-stage approach. The first stage encompassed the preparation of a ketone from 6-bromo-2-naphthol and 2-hydroxyethyl vinyl ether via Heck reaction. The palladium(0) complex was formed in situ and acted as the catalyst. In the second stage, the hydroxil group of 1-(6-hydroxynaphthalen-2-yl)ethan-1-on was substituted with a selected secondary amine (dimethylamine, piperidine or pyrrolidine) via Bucherer reaction. The reaction was performed in an autoclave. All three syntheses were carried out successfully.

• Keywords: Bucherer reaction, Heck raction, 2-naphthylamines, palladium catalyst