35143-08-9Relevant academic research and scientific papers
Visible-Light-Promoted Remote C-H Functionalization of o-Diazoniaphenyl Alkyl Sulfones
Du, Shaofu,Kimball, Elizabeth Ann,Ragains, Justin R.
supporting information, p. 5553 - 5556 (2017/10/25)
Visible-light irradiation of ortho-diazoniaphenyl alkyl sulfones in the presence of Ru(bpy)32+ results in remote Csp3-H functionalization. Key mechanistic steps in these processes involve intramolecular hydrogen atom transfer from Csp3-H bonds to aryl radicals to generate alkyl/benzyl radicals. Subsequent polar crossover occurs by single-electron oxidation of the alkyl/benzyl radicals to carbenium ions that then intercept nucleophiles. We have developed remote hydroxylations, etherifications, an amidation, and C-C bond formation processes using this strategy.
Synthesis of aryl sulfides by decarboxylative C-S cross-couplings
Duan, Zhongyu,Ranjit, Sadananda,Zhang, Pengfei,Liu, Xiaogang
supporting information; experimental part, p. 3666 - 3669 (2009/12/07)
A study was conducted to demonstrate the transition-metal-catalyzed synthesis of aryl sulfides by decarboxylative C-S cross-couplings. Coupling reaction of 2-nitrobenzoic acid with 1-octanethiol were carried in the presence of different combinations of tr
The different electronic natures displayed by the alkylthio groups in simple and higher conjugated aniline systems
Han, Chien-Chung,Balakumar,Thirumalai,Chung, Ming-Tsu
, p. 3511 - 3516 (2008/09/17)
Systematic studies based on 1H NMR and 13C NMR indicated that the alkylthio group behaves as a weak electron-withdrawing group in a simple aniline system like 2-butylthioaniline, while the same alkylthio group clearly acted as a resonance electron-donating group in higher conjugated aniline trimer systems, like butylthio-substituted PDA (mono-PDA) and dibutylthio-substituted PDA (2,6-diPDA). The formation of 2,6-diPDA as the major byproduct during the preparation of mono-PDA from PDI and butane-1-thiol provided additional support for the resonance electron donating nature of the butylthio group in these aniline trimer systems. Furthermore, CV studies also clearly indicated that the redox potential E° (vs. SCE) of the aniline trimer systems decreased with the increase in the number of butylthio groups, further confirming the electron-donating nature of the butylthio group in these higher conjugated trimer systems. The Royal Society of Chemistry 2006.
KF-alumina immobilized in ionic liquids: A novel heterogeneous base for heterocyclization of alkylsulfanylphenylamines into 1,4-benzothiazine
Chhikara, Bhupender S.,Mishra, Anil K.,Tandon, Vibha
, p. 1057 - 1065 (2007/10/03)
A rapid and convenient synthetic methodology for the cyclocondensative transformation of various alkylsulfanylphenylamines with bromoacetyl bromide by supporting on KF-alumina in ionic liquids [bmim] [Br] and [bmim][BF 4] has been developed to obtain 3-oxo-1,4-benzothiazine in good yields. The product is easily obtained by extraction with ethyl acetate and concentrating under vacuum. Easy recovery of ionic liquid and use in consecutive reactions is also reported.
Alkyl- or arylthiolation of aryl iodide via cleavage of the S-S bond of disulfide compound by nickel catalyst and zinc
Taniguchi, Nobukazu
, p. 6904 - 6906 (2007/10/03)
Various aryl sulfides can be synthesized by nickel-catalyzed alkyl- or arylthiolation of aryl iodide with a disulfide compound. This reaction produces Ni(0) from NiBr2-bpy by the reduction with zinc, and this generated complex works as an activating species to convert ArI into ArSR under neutral conditions. Furthermore, this system enables the use of two RS groups in (RS)2.
Synthesis of 4-(Phenylamino)quinoline-3-carboxamides as a novel class of gastric H+/K+-ATPase inhibitors
Uchida,Otsubo,Matsubara,Ohtani,Morita,Yamasaki
, p. 693 - 698 (2007/10/03)
In a search for inhibitors of gastric H+/K+-ATPase, 4-(phenylamino)quinoline-3-carboxamides were synthesized and evaluated for antisecretory activity against histamine-induced gastric acid secretion in rats. These compounds were synt
Reaction of Phenylnitrenium Ion with Sulphides. A Novel Synthetic Method for Aminophenyl Sulphide Derivatives
Takeuchi, Hiroshi,Hirayama, Shinji,Mitani, Michiharu,Koyama, Kikuhiko
, p. 521 - 528 (2007/10/02)
The reaction of phenyl azide with sulphides in the presence of both trifluoroacetic acid and trifluoromethanesulphonic acid to produce 2- and 4-aminophenyl sulphides (2) and (3) was investigated in order to obtain information on the following points: the kinetics of decomposition of phenyl azide, the effect of addition of benzene to reaction systems, the replacement of phenyl azide by 1-phenyl-2-methyl-4,6-diphenylpyridinium salt, and the steric and electronic effect of substituents in the sulphides.The products are formed through an azasulphonium ion by reaction of phenylnitrenium ion with sulphide, followed by rearrangement of the alkyl group in the azasulphonium ion.Sulphides with primary alykl groups larger than propyl result in selective formation of ortho-products (2), the mechanism of which is discussed in detail.
Alkylation of Benzothiazolines and the Stevens Rearrangement of the Resulting 2,3,3-Trisubstituted Benzothiazolinium Salts
Akiba, Kin-ya,Ohara, Yoshio,Inamoto, Naoki
, p. 2976 - 2983 (2007/10/02)
Alkylation of 2-substituted 3-methyl- or 3-ethylbenzothiazolines with Meerwein reagents gave 2-substituted 3,3-dialkylbenzothiazolinium tetrafluoroborates (3).The configuration of two alkyl groups on the nitrogen was assigned by NMR spectra and NOE measurement.In the Stevens rearrangement of 3 with lithium diisopropylamide ethyl group showed a much larger migratory aptitude (Et:Me>20:1) than methyl group irrespective of the configuration of 3, and cyclic ammonium ylide with planar ?-type carbanion was proposed as an intermediate. 3 suffered nucleophilic attack at the ring sulfur atom by butyllithium to afford a ring-opened ammonium ylide, which collapses to a radical pair to give unusual Stevens rearrangement product, where o-alkylthiophenyl group migrated selectively in preference to alkyl group, because of stabilization by participation of o-alkylthio group.
