Discipline: Chemistry and Chemical Sciences
Subcategory: Chemistry (not Biochemistry)
Sheela Lewis - California State University, Bakersfield
Co-Author(s): Anna Avina, Tyler Carcamo, Walter Fuentes, Amandeep Sidhu, Luis Salazar, and Raymond Carag-Chiu, California State University of Bakersfield, Bakersfield, CA
Isoxazolines are five membered nitrogen and oxygen bearing rings that contribute to the stability and function of pharmaceutical and pesticide agents. These molecules are widely synthesized for their significant biological properties such as antibacterial, anticancer, and anti-inflammatory activity. Isoxazolines are commonly synthesized via a reaction between nitrile oxides and dipolarophiles that utilize toxic, carcinogenic solvents. The proposed research focuses on developing an environmentally benign, faster, one-pot formation of isoxazolines. Recent work has met these goals with favorable results. A one-pot, greener synthetic route using surfactants in aqueous media was developed to prepare isoxazolines achieving yields as high as 77%. With the established optimal yield and reaction conditions, various aldehydes and dipolarophiles are currently being tested to determine the reaction scope. This research provides a more efficient, environmentally friendly method for the synthesis of isoxazolines and will advance the field of organic synthesis to utilize surfactants and develop greener methods.
Funder Acknowledgement(s): This project is supported in part by NSF grant under HRD-0331537 (CSU-LSAMP), NSF grant MMRI 122930, and the Ronald E. McNair Postbaccalaureate Achievement Program.
Faculty Advisor: Danielle Solano,