Abstract
To demonstrate the simplicity of adopting solid-phase synthesis of heterocycles by novices, we developed an appropriate education module (3 weeks in length) for the second-year undergraduate Organic Chemistry laboratory that effectively introduced solid-phase synthesis into the undergraduate curriculum. Starting with Wang resin, a four-step synthesis involving a 2-nitrobenzenesulfonamide intermediate and two points of chemical diversity produced a ten compound library of indazole 1-oxides in good yield. Cleavage of the final resin construct with 50% TFA/DCM provided each student with a sample of their unique compound. Four short instructional video clips supplement the laboratory activities described in this chapter.
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Acknowledgment
This work was supported by the Chemistry Department, Kalamazoo College; and the author wishes to thank Dr. Laura Furge, Chemistry Department, Kalamazoo College for her work in the instructional laboratories; and additional support for this project in part by a grant to Kalamazoo College from the Howard Hughes Medical Institute through the Precollege and Undergraduate Science Education Program.
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Slough, G.A. (2017). Solid-Phase Synthesis of Heterocycles in Practice. In: Krchňák , V. (eds) Solid-Phase Synthesis of Nitrogenous Heterocycles. Topics in Heterocyclic Chemistry, vol 52. Springer, Cham. https://doi.org/10.1007/7081_2016_3
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DOI: https://doi.org/10.1007/7081_2016_3
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