Synthesis of Sulfonimidamides from Sulfenamides via an Alkoxy-amino-λ6 -sulfanenitrile Intermediate

Angewandte Chemie
Edward L BriggsJames A Bull

Abstract

Sulfonimidamides are intriguing new motifs for medicinal and agrochemistry, and provide attractive bioisosteres for sulfonamides. However, there remain few operationally simple methods for their preparation. Here, the synthesis of NH-sulfonimidamides is achieved directly from sulfenamides, themselves readily formed in one step from amines and disulfides. A highly chemoselective and one-pot NH and O transfer is developed, mediated by PhIO in iPrOH, using ammonium carbamate as the NH source, and in the presence of 1 equivalent of acetic acid. A wide range of functional groups are tolerated under the developed reaction conditions, which also enables the functionalization of the antidepressants desipramine and fluoxetine and the preparation of an aza analogue of the drug probenecid. The reaction is shown to proceed via different and concurrent mechanistic pathways, including the formation of novel S≡N sulfanenitrile species as intermediates. Several alkoxy-amino-λ6 -sulfanenitriles are prepared with different alcohols, and shown to be alkylating agents to a range of nucleophiles.

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Citations

May 20, 2020·Chemistry : a European Journal·Stephanie GreedJames Adam Bull
Apr 30, 2020·Chemical Reviews·Elżbieta Wojaczyńska, Jacek Wojaczyński
May 19, 2021·The Journal of Organic Chemistry·Gregory B CravenAlan Armstrong
Aug 26, 2020·Journal of the American Chemical Society·Thomas Q DaviesMichael C Willis
Sep 15, 2021·Chemistry : a European Journal·Michael AndresiniRenzo Luisi
Jul 3, 2021·Expert Opinion on Drug Discovery·Michael J Tilby, Michael C Willis
Nov 9, 2021·Journal of the American Chemical Society·Chunngai HuiAndrey P Antonchick

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