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- Title
A New, Practical One-Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides.
- Authors
Izzo, Flavia; Schäfer, Martina; Stockman, Robert; Lücking, Ulrich
- Abstract
Unprotected tertiary sulfonimidamides have been prepared in good to excellent yields in a one-pot transformation from tertiary sulfinamides through NH transfer. The reaction is mediated by commercially available (diacetoxyiodo)benzene and ammonium carbamate in methanol under convenient conditions. A wide range of functional groups are tolerated and initial results indicate that the NH transfer is stereospecific. A small molecule X-ray analysis of NH sulfonimidamide 2 a and its behavior in selected in vitro assays in comparison to the matched sulfonamide are also reported. This new reaction provides a safe, short and efficient approach to sulfonimidamides, which have been the subject of recent, growing interest in the life sciences.
- Subjects
SULFOXIMINES; CHEMICAL synthesis; STEREOSPECIFICITY; NITROGEN compound synthesis; ELECTROPHILIC substitution reactions
- Publication
Chemistry - A European Journal, 2017, Vol 23, Issue 60, p15189
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201703272