Sinteza organokatalizatorjev na osnovi kinuklidina

Mezek, Uroš (author), Grošelj, Uroš (mentor)

Iz 3,4-dietoksiciklobut-3-en-1,2-diona (1) in 3,5-bis(trifluorometil)anilina (4) sem uspešno pripravil skvaramat 5. Sinteza analognega skvaramata 3 iz 3,4-dietoksiciklobut-3-en-1,2-diona (1) in 3,5-bis(trifluorometil)benzilamina (2) ni bila uspešna. S katalitskim hidrogeniranjem alkena 6 sem pripravil aminski gradnik 7. Iz skvaramata 5 in aminskega gradnika 8 sem uspešno pripravil organokatalizator 3-((3,5-bis(trifluorometil)fenil)amino)-4-(((S)-kinolin-4-il((1S,2S,4S,5R)-5-vinilkinuklidin-2-il)metil)amino)ciklobut-3-en-1,2-dion (9). Vse produkte sem pripravil po postopkih iz literature.

• Language: Slovenian
• Keywords: organokatalizator, kinuklidin, kinolin, amin
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2020
• PID: 20.500.12556/RUL-115059
• COBISS.SI-ID: 1538567363
• Publication date in RUL: 10.04.2020

Secondary language

• Language: English
• Title: Synthesis of organocatalysts based on quinuclidine

Abstract

Squaramate 5 was prepared from 3,4-diethoxycyclobut-3-ene-1,2-dione (1) and 3,5-bis(trifluoromethyl)aniline (4). Synthesis of the analogous squaramate 3 from 3,4-diethoxycyclobut-3-ene-1,2-dione (1) and 3,5-bis(trifluoromethyl)benzylamine (2) was not successful. Catalytic hydrogenation of alkene 6 gave the amine building block 7. Starting from squaramate 5 and amine building block 8, the desired organocatalyst 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione (9) was synthesized. All the products were prepared following the literature procedures.

• Keywords: organocatalyst, quinuclidine, quinoline, amine