A New, Practical One‐Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides. Issue 60 (9th October 2017)

• Record Type: Journal Article
• Authors: Izzo, Flavia; Schäfer, Martina; Stockman, Robert; Lücking, Ulrich
• Is Part Of: Chemistry. Volume 23:Issue 60(2017)
• Page Start: 15189
• Page End: 15193
• Publication Date: 2017-10-09
• Subjects: drug design -- hypervalent iodine -- medicinal chemistry -- sulfinamides -- sulfonimidamides; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201703272
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : An NH transaction : The first direct synthesis of tertiary NH sulfonimidamides from tertiary sulfinamides by electrophilic NH transfer has been achieved. In vitro studies did not reveal any intrinsic flaw of the sulfonimidamide group regarding properties relevant to medicinal chemistry.