6667-19-2Relevant articles and documents
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.
Generation and reactions of thiirenium ions by the Cation Pool method
Shimizu, Akihiro,Horiuchi, Shun,Hayashi, Ryutaro,Matsumoto, Kouichi,Miyamoto, Yu,Morisawa, Yusuke,Wakabayashi, Tomonari,Yoshida, Jun-Ichi
, p. 97 - 113 (2018/02/07)
Thiirenium ions generated and accumulated by low-temperature electrochemical oxidation of disulfides in the presence of alkynes were successfully observed by low-temperature NMR, Raman, and mass spectroscopies and were found to be stable at temperatures below -40 °C. The thiirenium ions showed ambident reactivity toward subsequently added nucleophiles to give either disubstituted alkenes or alkynes depending on the nature of the nucleophiles.
AlCl3-catalyzed insertion of isocyanides into nitrogen-sulfur bonds of sulfenamides
Shiro, Daisuke,Fujiwara, Shin-Ichi,Tsuda, Susumu,Iwasaki, Takanori,Kuniyasu, Hitoshi,Kambe, Nobuaki
supporting information, p. 1531 - 1534 (2015/03/14)
Lewis acid-catalyzed insertion of isocyanides 2 into nitrogen-sulfur bonds of sulfenamides 1 was developed. This method provided a convenient method for the synthesis of isothioureas 3. Among Lewis acids examined, AlCl3 brought about the best result. Acetic acid assisted one-pot preparation of unsymmetrical ureas was also described.
Copper-catalyzed formation of sulfur-nitrogen bonds by dehydrocoupling of thiols with amines
Taniguchi, Nobukazu
experimental part, p. 2670 - 2673 (2010/07/18)
Copper-catalyzed formation of sulfur-nitrogen bonds can be performed by a dehydrocoupling of aryl thiols with amines. Sulfenamides or sulfonamides can be produced by the use of a copper catalyst in air or under oxygen atmosphere. Furthermore, a reaction involving the combination of a palladium catalyst and a copper catalyst selectively afforded sulfinamides.
Copper-catalyzed synthesis of sulfenamides utilizing diaryl disulfides with alkyl amines
Taniguchi, Nobukazu
, p. 1917 - 1920 (2008/03/13)
The copper-catalyzed coupling of diaryl disulfides with alkyl amines can afford various sulfenamides in good yields. Furthermore, the present reaction is efficient and can be used for both of the aryl sulfide groups on disulfide. Georg Thieme Verlag Stutt
Imination of sulfur-containing compounds: XXXVI. A new method of synthesis and oxidative arylsulfonylimination of sulfenamides
Koval'
, p. 386 - 389 (2007/10/03)
Sulfenylation of ammonia, amines, and arenesulfonamide sodium salts with N-(arylsulfenyl)-N,N′-bis(arylsulfonyl)sulfinimidamides afforded unsubstituted and N-substituted arenesulfenamides. Oxidation of the latter with N-chloro sulfonamide sodium salts gav
A palladium-catalyzed regio- and stereoselective four-component coupling reaction
Knapton, Daniel J.,Meyer, Tara Y.
, p. 785 - 796 (2007/10/03)
(Chemical Equation Presented) Pd(PPh3)4 catalytically assembles sulfenamide, alkyne, carbon monoxide, and diphenyl diselenide regio- and stereoselectively in a one-pot four-component coupling reaction to yield (Z)-β-selenyl acrylamid
N-hydroxypyridine-2(1H)-thione derivatives of carboxylic acids as activated esters. Part I. The synthesis of carboxamides
Barton, Derek H. R.,Ferreira, J. Albert
, p. 9347 - 9366 (2007/10/03)
The reaction between an acyl derivative of N-hydroxypyridine-2(1H)- thione (a Barton PTOC ester) and either an amine (primary or secondary), or the corresponding sulfenamide, led to the formation of a carboxamide in a clean transformation requiring minimal work-up and purification. The reaction with a sulfenamide is particularly useful since the only by-product, an unsymmetrical disulfide, is of both synthetic and biological value. In sterically demanding cases, Barton PTOC esters were more reactive towards benzenesulfenamides than to the corresponding free amines.
Carbon-13, Nitrogen-15, Oxygen-17 and Sulphur-33 NMR Chemical Shifts of Some Sulphur Amides and Related Compounds
Haakkinen, A.-M.,Ruostesuo, P.
, p. 424 - 427 (2007/10/02)
15N, 17O and 33S NMR chemical shifts were determined for some aliphatic and aromatic sulphonamides, sulphinamides, sulphenamides and related sulphones and sulphoxides.The 17O and 33S NMR chemical shifts change only slightly for the sulphonyl compounds.In the sulphinyl compounds, on the other hand, the presence of nitrogen causes a noticeable shift to higher frequencies in the 17O resonance.The differences between the 17O chemical shifts of sulphinyl and sulphonyl compounds are more noticeable than those between sulphinamides and sulphoxides.The 15N NMR chemical shifts of sulphon-, sulphin- and sulphenamides reflectbwell the effect of the environments of both nitrogen and the adjacent sulphur atom.The correlations between 15N, 17O and 33S NMR chemical shifts and the structures of sulphur amides and related sulphones and sulphoxides are discussed.The chemical shifts of the 13C nuclei are also presented.
