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Solid-Phase Synthesis of Heterocycles in Practice

  • Greg A. SloughEmail author
Chapter
  • 486 Downloads
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 52)

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.

Keywords

Crosslinked polystyrene Hands-on learning Indazole 1-oxide Instructional module Linker Second-year undergraduate Solid-phase stoichiometry Solid-phase synthesis 

Notes

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.

Supplementary material

426537_1_En_3_MOESM1_ESM.mp4 (42.3 mb)
Video 1. (MP4 43314 kb)
426537_1_En_3_MOESM2_ESM.mp4 (49.6 mb)
Video 2. (MP4 50743 kb)
426537_1_En_3_MOESM3_ESM.mp4 (46.4 mb)
Video 3. (MP4 47510 kb)
426537_1_En_3_MOESM4_ESM.mp4 (25.1 mb)
Video 4. (MP4 25677 kb)

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Copyright information

© Springer International Publishing AG 2017

Authors and Affiliations

  1. 1.Chemistry DepartmentKalamazoo CollegeKalamazooUSA

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