3206-48-2Relevant articles and documents
One-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols
Ando, Kaori,Hattori, Junichiro
, (2019)
A method for one-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols and thiols is reported. A variety of primary alcohols were converted to the corresponding mesylates by methansulfonyl chloride and triethylamine in THF. After the reaction is complete, thiol (1 or 10) and either NaH or t-BuOK were added. The Julia-Kocienski sulfides 3, 9 and 11 were prepared by one-pot two steps procedure from alcohols in 76–96% yields (16 examples). Furthermore, after the sulfide formation, the reaction mixture was neutralized by p-toluenesulfonic acid and treated with H2O2 and ammonium molybdate in EtOH to give the Julia-Kocienski sulfones 4 in good yields except for trans-2-hexen-1-ol.
Synthesis, antibacterial and QSAR evaluation of 5-oxo and 5-thio derivatives of 1,4-disubstituted tetrazoles
Morjan, Rami Y.,Al-Attar, Nisreen H.,Abu-Teim, Omar S.,Ulrich, Maschke,Awadallah, Adel M.,Mkadmh, Ahmed M.,Elmanama, Abdelrauof A.,Raftery, James,Abu-Awwad, Fakhr M.,Yaseen, Zyad J.,Elqidrea, Ammar F.,Gardiner, John M.
, p. 4024 - 4028 (2015/08/24)
Abstract A series of 1,4-disubstituted tetrazol-5-ones 3a, 5, 7, 12, 13 and 1,4-disubstituted tetrazol-5-thiones 3b, 9, 10 was synthesized and fully characterized by IR, MS, 1H NMR and 13C NMR. The series was evaluated for in vitro antibacterial activity against four Gram negative (Escherichia coli, Proteus mirabilis, Klebsiella pneumonia, and Pseudomonas aeruginosa) and three Gram positive (Staphylococcus aureus, Enterococcus faecalis, and Bacillus subtilis) bacteria. The zone of inhibition was measured using the well-diffusion assay, and in vitro minimum inhibitory concentration (MIC) was determined by microbroth dilution assay. MIC values indicate that compounds exhibited a varied range (0.2-37 μg/mL) of antibacterial activity against the tested bacterial strains. Statistically significant QSAR models were developed by the simple linear regression analysis for the correlation of MIC with computed descriptors. The concluded cross validated regression factors are 0.953 and 0.986 for E. coli, and S. aureus, respectively.
Alkylation of thiols with trichloroacetimidates under neutral conditions
Duffy, Brian C.,Howard, Kyle T.,Chisholm, John D.
, p. 3301 - 3305 (2015/03/04)
Trichloroacetimidates are displaced with thiols to form the corresponding sulfides without the need for an added acid or base by simply heating the reactants in refluxing THF. This operationally simple procedure provides the corresponding sulfides in excellent yields with only the formation of the neutral trichloroacetamide as the side product. The imidate may also be formed in situ, allowing for a direct method for the formation of sulfides from alcohols. This reaction provides a general method for the synthesis of a variety of sulfides from inexpensive and readily available alcohol starting materials.