142-04-1Relevant articles and documents
Synthesis of N-Aryl-3,5-dichloro-4H-1,2,6-thiadiazin-4-imines from 3,4,4,5-Tetrachloro-4H-1,2,6-thiadiazine
Kalogirou, Andreas S.,Manoli, Maria,Koutentis, Panayiotis A.
, p. 4118 - 4121 (2015)
Condensation of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine with a range of anilines gave 22 N-aryl-3,5-dichloro-4H-1,2,6-thiadiazin-4-imines in 43-96% yields. The scope and limitations of this condensation are briefly investigated. Furthermore, mono- and bis-substitution of the C-3 and C-5 chlorines of 3,5-dichloro-N-phenyl-4H-1,2,6-thiadiazin-4-imine by amine and alkoxide nucleophiles is explored. Finally, Stille coupling chemistry is used to prepare several N-phenyl-3,5-diaryl-4H-1,2,6-thiadiazin-4-imines.
The biosynthesis of ephedrine
Grue-Sorensen,Spenser
, p. 998 - 1009 (1989)
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Ethoxydeamination of α-phenylaminobenzylphosphonate derivatives [4]
Ismagilov,Moskva,Ofitserov,Shamsutdinova
, p. 818 - 819 (2002)
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Iron-catalyzed selective reduction of nitro compounds to amines
Pehlivan, Leyla,Métay, Estelle,Laval, Stéphane,Dayoub, Wissam,Demonchaux, Patrice,Mignani, Gérard,Lemaire, Marc
, p. 1939 - 1941 (2010)
An efficient reduction of the nitro group with a catalytic amount of Fe(acac)3 and TMDS in THF at 60 °C affording the corresponding amine is described.
Synthesis and experimental and theoretical characterization of m-fluorosulfinylaniline
Páez Jerez, Ana L.,Chemes, Doly M.,Cutin, Edgardo H.,Oberhammer, Heinz,Robles, Norma L.
, p. 4445 - 4451 (2015)
The synthesis of m-fluorosulfinylaniline together with a tentative assignment of the vibrational, NMR and mass spectra are reported. Quantum chemical calculations predict two stable conformers, with very similar energies, both of which possess in the liquid phase syn structure of the -NSO moiety (syn of the SO double bond relative to the C-N single bond). Both conformers belong to the CS symmetry group and differ by the relative orientation of the fluorine atom and the NSO group. However, the FT-IR, FT-Raman and NMR spectra do not allow a distinction between these two conformers. The experimentally observed spectral data (FT-IR, FT-Raman, 1H and 13C and GC-mass spectrometry) of the title compound are compared with the spectral data obtained by quantum chemical calculations and the gauge including atomic orbital (GIAO) method (DFT/B3LYP approximation using 6-311+G(df), 6-311++G(df,pd) and cc-pVTZ basis sets). Moreover, natural bond orbital (NBO) analysis is applied for studying the stability of the molecule upon charge delocalization in order to provide an explanation of its electronic properties.
Solvent-freeN-Boc deprotection byex situgeneration of hydrogen chloride gas
De Borggraeve, Wim M.,Gilles, Philippe,Van Mileghem, Seger,Verschueren, Rik H.
, p. 5782 - 5787 (2021/07/12)
An efficient, scalable and sustainable method for the quantitative deprotection of thetert-butyl carbamate (N-Boc) protecting group is described, using down to near-stoichiometric amounts of hydrogen chloride gas in solvent-free conditions. We demonstrate theex situgeneration of hydrogen chloride gas from sodium chloride and sulfuric acid in a two-chamber reactor, introducing a straightforward method for controlled and stoichiometric release of HCl gas. The solvent-free conditions allow deprotection of a wide variety ofN-Boc derivatives to obtain the hydrochloride salts in quantitative yields. The procedure obviates the need for any work-up or purification steps providing an uncomplicated green alternative to standard methods. Due to the solvent-free, anhydrous conditions, this method shows high tolerance towards acid sensitive functional groups and furnishes expanded functional group orthogonality.
Selective and Additive-Free Hydrogenation of Nitroarenes Mediated by a DMSO-Tagged Molecular Cobalt Corrole Catalyst
Sch?fberger, Wolfgang,Timelthaler, Daniel,Topf, Christoph
supporting information, p. 2114 - 2120 (2021/07/22)
We report on the first cobalt corrole that effectively mediates the homogeneous hydrogenation of structurally diverse nitroarenes to afford the corresponding amines. The given catalyst is easily assembled prior to use from 4-tert-butylbenzaldehyde and pyrrole followed by metalation of the resulting corrole macrocycle with cobalt(II) acetate. The thus-prepared complex is self-contained in that the hydrogenation protocol is free from the requirement for adding any auxiliary reagent to elicit the catalytic activity of the applied metal complex. Moreover, a containment system is not required for the assembly of the hydrogenation reaction set-up as both the autoclave and the reaction vessels are readily charged under a regular laboratory atmosphere.
Synthesis, characterization and electropolymerization of functionalized organic salt–anilinium saccharinate and electrochemically controlled release of saccharinate anions
Shen, Lanbo,Gao, Na,Huang, Xirong
, (2019/11/03)
In this work, a novel functionalized organic salt ? anilinium saccharinate ([HANI][Sac]) was synthesized by the ion exchange method, and its composition and properties were characterized by 1H NMR, 13C NMR, ESI/MS and TG-DSC techniques. [HANI][Sac] can be used as both monomer and supporting electrolyte for efficient electrosynthesis of polyaniline (PANI) in acetonitrile. The obtained PANI has hierarchical porous structure and its doping degree with saccharinate anion ([Sac]-) is as high as 33.5%. The resulting [Sac]--doped-PANI (PANI-[Sac]) can be used as an electrochemically controlled drug delivery system. The in vitro release kinetics of [Sac]- under different potential stimuli conditions showed that, at a given time, the release rate of [Sac]- and its release percentage (ratio of the amount released to that loaded) increase with the negative shift of the applied potential. The amount of [Sac]- loaded and/or released can also be regulated by varying the charge for PANI electropolymerization. The present work provides a new strategy for the facile construction of conducting polymer-based electrochemically controlled drug release system.
