1455-91-0Relevant articles and documents
SH-methylation of SH-containing heterocycles with dimethyl carbonate via phase-transfer catalytic reaction
Xie, Jian-Gang,Quan, Jing,Li, Shu-Bai,Zheng, Yan,Zhu, Li-Min
experimental part, p. 871 - 878 (2011/04/22)
A reaction of SH-containing heterocycles with dimethyl carbonate (DMC) in the presence of K2CO3 and tetrabutylammonium bromide (Bu4NBr) gave heteroaryl methyl thioethers in 44-93% yields. The reaction was carried out under mild conditions. This method provided a useful synthetic method for preparation of various heteroaryl methyl thioethers without the use of toxic methylic halides or dimethyl sulfate.
Electronic properties of 1-methyl-4-phenyl-1H-tetrazole-5(4H)-thiones: An experimental and theoretical study
Rayat, Sundeep,Chhabra, Radhika,Alawode, Olajide,Gundugola, Aditya S.
experimental part, p. 38 - 45 (2010/02/16)
The syntheses of 1-(4-methoxyphenyl)-4-methyl-1H-tetrazol-5(4H)-thione 1a, 1-methyl-4-phenyl-1H-tetrazole-5(4H)-thione 1b, 1-(4-chlorophenyl)-4-methyl-1H-tetrazol-5(4H)-thione 1c, 1-methyl-4-(4-nitrophenyl)-1H-tetrazol-5(4H)-thione 1d were carried out and their electronic absorption spectra were obtained in cyclohexane, THF, and acetonitrile. The UV spectra of 1a-d showed a modest dependence on the polarity of the solvent. The change of substituent on the tetrazolethione ring from a strongly electron donating group (p-C6H4OMe, 1a), to a moderately electron donating (C6H5, 1b) to a weakly electron withdrawing group (p-C6H4Cl, 1c) also produced minimal effect on the electronic properties of 1a-c. However, the presence of a strongly electron withdrawing group (p-C6H4NO2, 1d) on the heterocyclic ring produced a marked change in the UV spectrum. Time-dependent density functional calculations revealed that all the bands result from π → π* excitations with some degree of intramolecular charge transfer (ICT) within the molecules. Our studies further showed that as the acceptor strength is increased in the order: 1a (p-C6H4OMe) 6H5) 6H4Cl) 6H4NO2), the ICT also increases. In accordance with the experimental observations, the calculated transitions also showed modest dependence on the polarity of the solvent.
Photoextrusion of Nitrogen from 1,4-Dihydro-1-phenyl-5H-tetrazol-5-ones and -thiones. Benzimidazolones and Carbodiimides
Quast, Helmut,Nahr, Uwe
, p. 526 - 540 (2007/10/02)
Alkylation of 1-phenyltetrazolone 10a with 2-cyclohexen-1-yl bromide followed by dehydrogenation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone permits introduction of a phenyl group at N-4 of the tetrazole ring via the sequence 10a -> 10f -> 10g.The photoextrusion of molecular nitrogen from the (N-4)-substituted 1-phenyltetrazolones, 10a (hydrogen), 10b (methyl), 10d,e (propenyl), and 10g (phenyl) produces essentially quantitative yields of the corresponding benzimidazolones 14a,b,d,e,g.On irradiation of the 1-phenyltetrazolethiones 8b,f,g the carbodiimides 22b,f,g are obtained together with molecular nitrogen and sulfur, while 8a affords phenylcyanamide (25).In contrast to the thermolysis, which is known to give 2-(methylamino)benzothiazole (21b), photolysis of the (phenylimino)-1,2,3,4-thiatriazole 24, an isomer of methylphenyltetrazolethione 8b, also yields molecular nitrogen, sulfur, and methylphenylcarbodiimide (22b).