66168-29-4Relevant academic research and scientific papers
Transition-Metal-Free Thioamination of Arynes Using Sulfenamides
Gaykar, Rahul N.,Bhattacharjee, Subrata,Biju, Akkattu T.
supporting information, p. 737 - 740 (2019/01/25)
The insertion of arynes into the S-N σ-bond of sulfenamides allowing the synthesis of o-sulfanylaniline derivatives with reasonable functional group compatibility is presented. The aryne generated from 2-(trimethylsilyl)aryl triflates using CsF in DME was the key for the success of this transition-metal-free thioamination reaction, which involves new C-N and C-S bond formations in a single step under mild conditions. Moreover, the synthetic potential of this method was demonstrated by the synthesis of the antidepressant drug vortioxetine.
Synthesis of Sulfonimidamides from Sulfenamides via an Alkoxy-amino-λ6-sulfanenitrile Intermediate
Briggs, Edward L.,Tota, Arianna,Colella, Marco,Degennaro, Leonardo,Luisi, Renzo,Bull, James A.
supporting information, p. 14303 - 14310 (2019/09/06)
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.
Catalytic thia-Sommelet-Hauser rearrangement: Application to the synthesis of oxindoles
Li, Yuye,Shi, Yi,Huang, Zhongxing,Wu, Xinhu,Xu, Pengfei,Wang, Jianbo,Zhang, Yan
supporting information; experimental part, p. 1210 - 1213 (2011/04/27)
A series of 3-arylthio-1,3-disubstituted-oxindoles were prepared in good yields by the reaction of α-diazocarbonyl compounds and sulfenamides. The reaction involves a Rh-catalyzed thia-Sommelet-Hauser-type rearrangement.(Figure Presented)
LDA-promoted decomposition of benzenesulfenamides. A route to aminyl radicals by dioxygen oxidation of lithium amides
Barbieri, Anna,Montevecchi, Pier Carlo,Nanni, Daniele,Navacchia, Maria Luisa
, p. 13255 - 13264 (2007/10/03)
The LDA-promoted decomposition of N-monosubstituted sulfenamides 1a-d occurs through the formation of thioaminyl anions, which undergo oxidation either at sulfur, with formation of sulfonamides, or at nitrogen, with formation of thioaminyl radicals, depending on the nature of the 4'-substituent. The reaction of N,N-disubstituted sulfenamides 1e-h proceeds through the intermediacy of a lithium complex capable of generating aminyl radicals via sulfenyl group transfer to the di-iso-propylamido anion and subsequent aerial oxidation of the resulting lithium amides 3e-h.
The Reaction of Benzenesulfenanilides with Lewis Acids: Involvement of Radical Cation Intermediates.
Grossi, Loris,Montevecchi, Carlo
, p. 9095 - 9104 (2007/10/02)
The 4'-substituted N-methylbenzenesulfenanilides 1a-c react with Lewis acids, including BF3, AlCl3 and GaCl3, to afford the radical cation intermediates 9a-c, some of which could be detected by e.p.r. spectroscopy.Thus, the 4'-methoxy substituted compound 1a gave the fairly persistent radical cation 9a.In contrast, the radical cation 9b, derived from the 4'-nitro substituted compound 4b, was not detected apparently because it decayed too rapidly forming the very stable radical cation 11b, intermediate in the formation of the rearranged sulfide 10b.The radical intermediates 9a-c react with cyclohexene to give the 1,2-adducts 4a-c, 5 and 6 which are believed to be formed from either the thiiranium ion 7b or the sulfurane 8a,c.
