Sinteza in pretvorbe (E)-3-(fenilamino)-1-(4-klorofenil)prop-2-en-1-ona

Urbančič, David (author), Svete, Jurij (mentor)

V diplomskem delu sem v prvi stopnji sintetiziral enaminon 27 iz 4-kloroacetofenona (26) in DMFDMA. V naslednji stopnji sem nastali enaminon 27 spajal s primarnim in sekundarnim aminom. Kot sekundarni amin sem uporabil N-metilanilin (30), kot primarni pa alilamin (28). Slednjo reakcijo med alilaminom in enaminom 27 sem izvajal pod različnimi reakcijskimi pogoji, ter primerjal učinkovitost sinteze in regeneracije začetnega reagenta 27. Enaminon, sklopljen z alilaminom (29), sem uporabil še v zadnjih dveh ločenih reakcijah. V prvi reakciji sem spojino zaščitil na dušikovem atomu s t-butoksikarbonilno skupino, v drugi reakciji pa sem skušal na dušikov atom uvesti metilno skupino po Eschweiler-Clarke metodi, a sem namesto metiliranega produkta 33 dobil simetričen 1,4-dihidropiridin 34. Vse spojine, razen enaminona 27, sintetiziranega v prvi stopnji, še niso bile obravnavane v literaturi, zato smo jih okarakterizirali z 1H NMR, 13C NMR, IR in masno spektroskopijo, ter jim določili temperaturo tališča in elementno sestavo.

• Language: Slovenian
• Keywords: Enaminoni, amini, kondenzacija.
• 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-149679
• COBISS.SI-ID: 171461635
• Publication date in RUL: 08.09.2023

Secondary language

• Language: English
• Title: Synthesis and transformation of (E)-1-(4-chlorophenyl)-3-(phenylamino)prop-2-en-1-one

Abstract

In the first step of my thesis enaminone 27 was synthesised from 4-chloroacetophenone (26) and DMFDMA. In the next stage the produced enaminone was reacted with a primary and a secondary amine. N-Methylaniline (30) was used as the secondary amine and allylamine (28) as the primary amine. The latter reaction between allylamine (28) and enamine 27 was carried under different reaction conditions. Results were then compared in the overall efficiency of the synthesis and regeneration of the starting reagent 27. Enaminone coupled to the allylamine (29) was then used in the last two separate reactions. In the first reaction, compound 29 was protected at the nitrogen atom with a t-butoxycarbonyl group, and in the second reaction I tried to introduce a methyl group at the nitrogen atom via Eschweiler-Clarke method, but instead of the methylated product 33, a symmetrical 1,4-dihydropyridine 34 was obtained. All compounds, except for the enaminone 27 synthesised in the first step, have not yet been discussed in the literature, so they were characterised by 1H NMR, 13C NMR, IR, and mass spectroscopy, their melting points and elemental compositions were also measured.

• Keywords: Enaminones, amines, condensation.