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Published on: June 20, 2014
Sulfoximine and Triazine-Acid Adduct Behavior in Aqueous HPMC: A Fast and Convenient N‑Functionalization of
Dhanush Pradeep Chethikkattil1, Ashish Dusunge1, Michael Harmata1
1Department of Chemistry, University of Missouri, 601 S College Ave, Columbia, Missouri 65211, United States.
Abstract:
Sulfoximines are valuable scaffolds in pharmaceuticals, yet their aqueous-phase stability and reactivity remain underexplored. We report a systematic study of sulfoximine-carboxylic acid coupling in water using hydroxypropyl methylcellulose (HPMC) as a microenvironment. In situ 19F NMR revealed potential key intermediates and the critical role of LiCl in their stabilization in water. The optimized protocol tolerates diverse functional groups, operates under mild conditions, and scales efficiently. These findings enable efficient sulfoximine functionalization and provide mechanistic insights.
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