Dean, Ira (2025) Synthesis and Optimization of Di-Substituted Acridine Photo-organocatalysts. Bachelor's Research Project, Pharmacy.
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Abstract
Acridine photo-organocatalysts have shown great promise in a multitude of chemical reactions, but the main obstacle with acridine lies in their harsh synthesis conditions. This investigation employed a method of synthesis consisting of a 3-step process, namely an Ullmann reaction, cyclization and Boc addition. Using this, it aimed to synthesize dimethyl-9(10H)-acridone Boc compounds, as well as optimize their synthesis. Furthermore, conditions were screened for synthesis of the starting material of 2,7-diphenyl-9(10H)-acridone Boc, namely for 4-bromo-[1,1'-biphenyl]-3-carboxylic acid using Suzuki-Miyaura reaction. The synthesis was optimized by increasing the pH after cyclization to enable Boc addition, by decreasing reaction time for Boc addition from 18 hours to 4 hours, and upon finding two di-methylacridin-9(10H)-one compounds formed during the cyclization step their separation was optimized by being performed after Boc addition. Furthermore, a total of 5 distinct dimethyl-9(10H)-acridone Boc compounds were synthesized in scaled-up conditions with yields of 51-74%, each making at least 0.750 g of compound. Screening conditions for 4-bromo-[1,1'-biphenyl]-3-carboxylic acid did not succeed in synthesizing the compound of interest.
| Item Type: | Thesis (Bachelor's Research Project) |
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| Supervisor name: | Fodran, P. |
| Degree programme: | Pharmacy |
| Thesis type: | Bachelor's Research Project |
| Language: | English |
| Date Deposited: | 02 Jul 2025 09:57 |
| Last Modified: | 14 Jul 2025 09:51 |
| URI: | https://fse.studenttheses.ub.rug.nl/id/eprint/35460 |
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