Synthesis and characterization of 2-pyridylsulfur pentafluorides
Current approaches to prepare SF5-substituted heterocycles during the synthesis of targeted heterocyclic compounds require the use of SF5-functionalized aryl or alkyne reagents or SF5Cl as a source of the SF5 functional group. Herein we report that excess oxidative fluorination of 2,2' -dipyridyl disulfide with a KF/Cl2 /MeCN system leads to the formation of thirteen new 2-pyridylsulfur chlorotetrafluorides (2-SF4Cl-pyridines). These molecules are found to undergo further chlorine-fluorine exchange reactions by treatment with silver(I) fluoride enabling ready access to a series of ten new substituted 2-pyridylsulfur pentafluorides (2-SF5-pyridines). This is the first preparatively simple and readily scalable example of the transformation of an existing heterocyclic sulfur functionality to prepare SF5-substituted heterocycles.
NaClO2-mediated preparation of pyridine-2-sulfonyl chlorides and synthesis of chiral sulfonamides
A simple method to prepare azaarenesulfonyl chlorides by NaClO2-mediated oxidative chlorination of azaarenethiols have been developed, with water as the solvent. Easy purification by simple extraction and concentration gives the products in good yields. The azaarenesulfonyl chlorides readily undergo condensation with chiral amines to afford chiral sulfonamides.
Xu, Dong,Yang, Shiyi,Gao, Aijun,Yang, Zhanhui
p. 463 - 473
(2020/07/03)
Grignard-Reagent-Promoted Desulfonylation/Intramolecular Coupling for the Synthesis of 2-(1-Fluorovinyl)pyridines
A novel process involving Grignard-reagent-promoted desulfonylation/intramolecular coupling of readily available α-fluoro-α,β-unsaturated-(2-pyridyl)sulfones was realized that provided a series of polysubstituted 2-(1-fluorovinyl)pyridines in good yields. The intrinsic coordination between pyridine and Mg(II) along with the "negative fluorine effect"of the substrates should play the key role for the smooth transformation in the absence of transition-metal catalysts.
Modelling nucleophilic substitution at silicon in solution using hypervalent silicon compounds based on 2-thiopyridones
Halodimethylsilylmethyl derivatives of 2-thiopyridones have been prepared. The N-CH2 isomer is favoured with the 6-methylthiopyridone. 13C and 29Si chemical shifts have been used to calculate the extent of sulfur-silicon bond formation and the extent of pentacoordination. The results are consistent with the oxygen analogues and reveal that as expected sulfur is a poorer nucleophile than oxygen. The unsubstituted thiopyridone and the 5-trifluoromethyl derivative favour the S-CH2 isomer. Again the mapping of nucleophilic substitution by nitrogen is in line with sulfur and oxygen nucleophiles, but in this series nitrogen is a poorer nucleophile than expected. The results are discussed in terms of steric strain, the preferences for alkylation of the pyridones and the bond strength of coordination to silicon.
Bassindale, Alan R.,Parker, David J.,Taylor, Peter G.
p. 1059 - 1066
(2007/10/03)
The Synthesis and Some Reactions of Novel Pyridine-2(1H)-thiones
The use of methyl 3-mercaptopropionate for the conversion of halogenated pyridins to pyridine thiones and thiols is described, and limitations of the reaction discussed.S-Alkylation and oxidation reactions of the products from these reactions are reported.
Dunn, A. D.,Norrie, R.,L'Hostis, J.,Marjot, S.
p. 119 - 125
(2007/10/02)
7-(3-Substituted ureido) cephalosporins
Cephalosporin compounds with 3-substituted ureido or -thioureido group at position 7 and hydrogen or heterocyclicthiomethyl groups at position 3 are prepared. These compounds are antibacterial agents.
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(2008/06/13)
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