3915-60-4Relevant academic research and scientific papers
Copper pyrithione (CuPT)-catalyzed/mediated amination and thioarylation of (hetero)aryl halides: A competition
Cao, Ningtao,Song, Bao,Xie, Jianwei,Zhang, Jie
, (2021/11/08)
A facile method for the synthesis of N-arylheterocycles and di(hetero)aryl sulfides under mild condition is described. In these transformations, copper pyrithione (CuPT) was used as the copper catalyst for C─N coupling, while served as catalyst and coupled partner for C─S coupling with high yields and broad substrate tolerance. The S-arylation process was also utilized for the construction of valuable bioactive 2-sulfonylpyridine 1-oxide derivatives.
Synthesis of N-(Alkyloxy)pyridine-2(1H)-thiones: Alkylations of the Ambident Nucleophile Pyridine-2(1H)-thione N-Oxide and Attempted Isomerizations of 2-(Alkylthio)pyridine N-Oxide
Hay, Benjamin P.,Beckwith, Athelstan L. J.
, p. 4330 - 4334 (2007/10/02)
Two possible routes for the preparation of N-(alkyloxy)pyridine-2(1H)-thiones (1), namely, nucleophilic substitution of pyridine-2(1H)-thione N-oxide anion (5) and the thermal rearrangemet of isomeric 2-(alkylthio)pyridine N-oxides (6), have been investigated.The ambident nucleophilic anion 5 undergoes both O- and S-alkylation upon treatment with alkyl bromides, chlorides, mesylates, or triflates; the regioselectivity is influenced by the temperature and the nature of the solvent, counterion, alkyl group, and leaving group.Details of the synthesis and characterization of a number of N-(alkyloxy)pyridine-2(1H)-thiones (1) (alkyl = n-propyl, n-butyl, benzyl, neopentyl, methoxymethyl, isopropyl, cyclopentyl, cyclohexyl, and tert-butyl) and 2-(alkylthio)pyridine N-oxides (6) (alkyl = n-propyl, n-butyl, and benzyl) are reported.Attempts to prepare 1 from the thermal rearrangement of 6 were unsuccessful, as 6 proved to be the thermodynamically stable isomer; the benzyl sulfide 1c was converted into its isomer 6c upon heating.Preliminary studies show that this rearrangement occurs in competition with N-O bond homolysis and appears to be catalyzed by molecular oxygen.
Generation of Sulfenate Salts via Ipso-substitution of Azaheterocyclic Sulfoxides. First Preparation and Characterization of Sodium 2-Pyridinesulfenate
Furukawa, Naomichi,Konno, Yasuo,Tsuruoka, Masayuki,Fujihara, Hisashi,Ogawa, Satoshi
, p. 1501 - 1504 (2007/10/02)
2-Alkyl- or 2-aryl-sulfinylpyridine N-oxides undergo ipsosubstitution reaction with sodium ethoxide to afford sodium sulfenates which were converted soon to the corresponding sulfinates upon contact with oxygen.Sodium 2-pyridinesulfenate was prepared and characterized by FT-IR as the first example of stable sulfenate.
