Synthesis of Cyclobutanes Utilizing Green Chemistry
Primary Faculty Mentor’s Name
Koushik Banerjee
Proposal Track
Student
Session Format
Poster
Abstract
The reactions of cyclobutanes is a topic that has yet to be thoroughly studied due to the challenges of working with the strained molecule. Cyclobutanes have been used as synthetic analogs for several different amino acids and biomolecules because of their diverse chemical and biological properties. These cyclobutane based amino acids have been used as active ingredients in pain relievers, anti-viral agents and anti-bacterial agents. Oxetanocin, a cyclobutane nucleoside, has been a substance of recent interest due to its effectiveness as an HIV fighting agent. They are also used in drug synthesis for anti-inflammatories as well as synthesis of anti-cancer drug. A green method for creating cyclobutanes from trans-cinnamic acid derivatives has been previously developed. In this experiment, trans-4-(trifluoromethyl) cinnamic acid was synthesized utilizing a green Knoevenagel condensation. This reaction had a 78.1% yield. This is at par with similar systems for synthesizing trans-4-(trifluoromethyl) cinnamic acid. This method uses microwaves as opposed to refluxing, which reduces the environmental impact of performing the synthesis. Trans-4-(trifluoromethyl) cinnamic acid has a variety of uses. It has a high cytotoxicity to cancer cells including lung, prostate, colon and breast cancer cells. However, it has been used in applications outside of pharmaceutical and medical chemistry. It is also an effective agent in reducing the phytotoxicity of herbicides for mitigating areas impacted by excessive use of herbicides or areas affected by herbicide runoff, making it a potential remediation agent. The synthesized carboxylic acid was dimerized utilizing a solid state photoreaction for 120 hours, creating a cyclobutane. The percent conversion for this reaction was 82%. An investigation into an effective catalyst to increase the conversion of the dimerization is currently being conducted. This chiral cyclobutane can be used as a synthetic analog for a variety of purposes such as the pharmaceutical synthesis of drugs or synthesis of biomolecules. This method provides a green method for synthesizing both the monomer trans-4-(trifluoromethyl) cinnamic acid as well as its dimer.
Keywords
Green Chemistry, Cyclobutanes, Synthetic Analogs, Photochemistry
Location
Concourse and Atrium
Presentation Year
2015
Start Date
11-7-2015 10:10 AM
End Date
11-7-2015 11:20 AM
Publication Type and Release Option
Presentation (Open Access)
Recommended Citation
Winfield, DeMichael, "Synthesis of Cyclobutanes Utilizing Green Chemistry" (2015). Georgia Undergraduate Research Conference (2014-2015). 64.
https://digitalcommons.georgiasouthern.edu/gurc/2015/2015/64
Synthesis of Cyclobutanes Utilizing Green Chemistry
Concourse and Atrium
The reactions of cyclobutanes is a topic that has yet to be thoroughly studied due to the challenges of working with the strained molecule. Cyclobutanes have been used as synthetic analogs for several different amino acids and biomolecules because of their diverse chemical and biological properties. These cyclobutane based amino acids have been used as active ingredients in pain relievers, anti-viral agents and anti-bacterial agents. Oxetanocin, a cyclobutane nucleoside, has been a substance of recent interest due to its effectiveness as an HIV fighting agent. They are also used in drug synthesis for anti-inflammatories as well as synthesis of anti-cancer drug. A green method for creating cyclobutanes from trans-cinnamic acid derivatives has been previously developed. In this experiment, trans-4-(trifluoromethyl) cinnamic acid was synthesized utilizing a green Knoevenagel condensation. This reaction had a 78.1% yield. This is at par with similar systems for synthesizing trans-4-(trifluoromethyl) cinnamic acid. This method uses microwaves as opposed to refluxing, which reduces the environmental impact of performing the synthesis. Trans-4-(trifluoromethyl) cinnamic acid has a variety of uses. It has a high cytotoxicity to cancer cells including lung, prostate, colon and breast cancer cells. However, it has been used in applications outside of pharmaceutical and medical chemistry. It is also an effective agent in reducing the phytotoxicity of herbicides for mitigating areas impacted by excessive use of herbicides or areas affected by herbicide runoff, making it a potential remediation agent. The synthesized carboxylic acid was dimerized utilizing a solid state photoreaction for 120 hours, creating a cyclobutane. The percent conversion for this reaction was 82%. An investigation into an effective catalyst to increase the conversion of the dimerization is currently being conducted. This chiral cyclobutane can be used as a synthetic analog for a variety of purposes such as the pharmaceutical synthesis of drugs or synthesis of biomolecules. This method provides a green method for synthesizing both the monomer trans-4-(trifluoromethyl) cinnamic acid as well as its dimer.
