53973-76-5Relevant academic research and scientific papers
New route for the synthesis of N-alkyl-2-(phenylsulfonyl)anilines
Hossan, Aisha
, p. 570 - 573 (2017/03/16)
[Figure not available: see fulltext.] The main objective of this work was to study the rearrangement reactions of 1-alkyl-2-[(phenylsulfonyl)methyl]pyridinium iodides in the presence of various nucleophiles, leading to N-alkyl-2-(phenylsulfonyl)aniline derivatives. The best results were achieved with alkylammonium sulfites, leading to pyridine ring opening followed by recyclization to give diphenyl sulfone derivatives in up to 78% yields.
Synthesis of substituted diphenyl sulfones and their structure-activity relationship with the antagonism of 5-HT6 receptors
Ivachtchenko, Alexandre,Golovina, Elena,Kadieva, Madina,Mitkin, Oleg,Tkachenko, Sergei,Okun, Ilya
, p. 4614 - 4627 (2013/07/26)
Substituted diphenyl sulfones (10a-n) were synthesised, and the structures were confirmed by NMR, LC-MS and X-ray crystallography. Their antagonistic activities towards 5-HT6 receptor were assessed in a cell-based functional assay. Diphenyl sulfone 10a, in spite of being the smallest and simplest known sulfonyl-containing 5-HT6R antagonist, showed a strong potency (Ki = 1.6 μM). Its derivative with a methylamine substituent, 10g (N-methyl-2-(phenylsulfonyl)aniline), was ～66-times as active as diphenyl sulfone (Ki = 24.3 nM). Addition of a piperazinyl moiety in the para-position relative to the sulfonyl group in compound 10m (N-methyl-2-(phenylsulfonyl)-5-piperazin-1-ylaniline) led to a further 150-fold increase in potency (Ki = 0.16 nM) to block the serotonin-induced response of HEK-293 cells that were stably transfected with the human recombinant 5-HT6 receptor.
Electron beam-induced fries rearrangement of sulfonamide and sulfonate crystals
Kato, Jun,Maekawa, Yasunari,Yoshida, Masaru
, p. 266 - 267 (2007/10/03)
The electron beam (EB) sensitivity of sulfonic acid derivatives in the crystalline state was much higher than that of the corresponding carboxylic acid derivatives, which was distinct from the results using other energy sources such as heat and UV; especially, sulfonamide derivatives could undergo the chemoselective Fries rearrangement to give ortho and para products in the ratio of ca. 7/3 without the meta isomer. Copyright
Intermediacy of o-sulfonylium arenide ylides in the reactions of arenesulfonyl derivatives with strong bases: Insight into the puzzling rearrangement of N-arylarenesulfonamides into 2-aminodiaryl sulfones
Eisch, John J.,Qian, Yun,Chiu, Chingchen S.
, p. 1392 - 1398 (2007/10/03)
Benzenesulfonyl derivatives, PhSO2E, such as benzenesulfonyl fluoride, phenyl benzenesulfonate, and N-methyl-N-phenylbenzenesulfonamide, have been found to undergo ortho-lithiation with lithium 2,2,6,6-tetramethylpiperidide (LTMP) in THF at -78 °C. The resulting lithio derivatives undergo 1,3-elimination of LiE to form the transient o-sulfonylium benzenide. The latter ylide, which may be stabilized by its carbenoid character and its complexation with LiE, can be trapped by benzophenone acting as a 1,3-dipolarophile to form the adduct, 3,3-diphenyl-1,2-benzoxathiole 1,1-dioxide. The alternative formation of the latter cyclic sulfonate by reaction of the initially formed o-lithio derivative with benzophenone and by subsequent cyclization was shown not to occur. If not trapped with benzophenone, such an ylide decomposes partly into SO2 and benzyne and then undergoes self-condensation to yield poly(phenylene-o,o′-biphenylene sulfones). o-Sulfonylium benzenide also can be captured by lithium alkoxides, either present adventitously or intentionally added, to generate the corresponding alkyl benzenesulfonate. However, such alkoxides, unaided by LTMP, are themselves unable to extract an ortho-proton from benzenesulfonyl fluoride or from N-methyl-N-phenylbenzenesulfonamide to yield the corresponding o-lithio derivative. With benzenesulfonyl fluoride the lithium alkoxide can also form the sulfonate ester by direct substitution at the sulfonyl group. The Closson-Hellwinkel rearrangement of N-methyl-N-phenylbenzenesulfonamide into o-(methylamino)diphenyl sulfone by RLi or LTMP is reinterpreted as proceeding by way of the 2-lithio- or 2,6-dilithiobenzenesulfonyl derivative which eliminates lithium N-methylanilide to form the o-sulfonylium benzenide or its 6-lithio derivative. Attack of the latter ylide, acting as an electrophile, upon the ortho-position of the presumably complexed LiNMePh then consummates the rearrangement.
