Catechol reactivity: Synthesis of dopamine derivatives substituted at the 6-position |
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Authors: | Jennifer C. Rote Sarah N. Malkowski C. Skyler Cochrane Gabrielle E. Bailey Noah S. Brown Mauricio Cafiero |
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Affiliation: | Department of Chemistry, Rhodes College, Memphis, TN, USA |
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Abstract: | Dopamine is a ubiquitous neurotransmitter essential in the proper functioning of the human body. In addition to this critical role, the catecholamine core has shown utility as a scaffold for numerous drugs and in other applications, like metal detection and adhesive materials. Substituents at the 6-position of dopamine’s catechol core can modulate its stereoelectronic properties, the acidity of its phenolic hydroxyl groups, and the overall hydrophobicity of the molecule. Herein, we report the synthesis of a series of four novel dopamine analogues substituted at the 6-position of catechol core. The 1H NMR chemical shift of the aromatic proton meta to the substituent correlated strongly with the Hammett σm constant, confirming the electronic properties of substituents. |
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Keywords: | Boron tribromide catecholamine dopamine Hammett constant O-demethylation |
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