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Towards the Synthesis of an Analog of Betanin

By Abigail Noble

Abstract

This research concentrated on furthering the development of an analog of the beet dye betanin. The development of this analog will allow for studies of its reactions with nucleophiles, specifically thiols, to understand how they might affect the degradation of the dye. This research explored methods to replace an N,N,N'-trimethylsemicarbazide group with a proline on our analog. Benzaldehyde N,N,N'-trimethylsemicarbazide (5) was synthesized to mimic the reaction. Experiments were run to synthesize benzaldehyde proline immine (4) simply and unambiguously. From these experiments, there is reason to believe that (4) is a stable molecule. Initial efforts in this Schiff base transfer equilibrium involved removing the semicarbazide as a glyoxal semicarbazone (8). This has not yet proved successful. A reaction was investigated that could remove the N,N,N'-trimethylsemicarbazide group from the starting model before adding the proline. These experiments were successful, and now a two-step reaction to form the desired product (4) is possible. With the completion and success of this set of reactions, a positive procedure may be designed in the future to test with the betanin analog

Year: 2004
OAI identifier: oai:triceratops.brynmawr.edu:10066/14275
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