1122-82-3Relevant articles and documents
Rhodium-catalyzed synthesis of isothiocyanate from isonitrile and sulfur
Arisawa, Mieko,Ashikawa, Masanori,Suwa, Atsushi,Yamaguchi, Masahiko
, p. 1727 - 1729 (2005)
Rhodium complexes RhH(PPh3)4 and Rh(acac)(CH 2CH2)2 catalyze sulfuration of isonitrile with sulfur giving isothiocyanates in high yields. The metal-catalyzed reaction is rapid in refluxing acetone, and completes within 3 h in most cases. The reaction exhibits induction period, which disappeared by preheating sulfur in refluxing acetone for 1.5 h. Use of several organic polysulfides in this transformation was examined in order to compare the reactivity.
Novel isothiocyanate transposition in 2-alkyliminothiazoles: a simple solution for regiochemical problem
Shin, Dongyun,Lee, Jihoon,Nam, Kee Dal,Hahn, Hoh-Gyu
, p. 3089 - 3092 (2007)
Novel alkyl/aryl transposition in the reaction of 2-iminothiazoles with alkyl/aryl isothiocyanates was found out, and the reaction was very easy to handle and gave good to excellent chemical yields. Moreover, transposition reaction provided a simple but excellent solution for regiochemical problems in 2-iminothiazole synthesis.
ACID CATALYSIS OF THE DENITROSATION OF N-METHYL-N prime -CYCLOHEXYL-N-NITROSOTHIOUREA.
Isobe
, p. 601 - 602 (1984)
The kinetics of denitrosation of N-methyl-N prime -cyclohexyl-N-nitrosothiourea has been studied in the range of pH 3. 45-3. 73 using four organic acids; acetic acid, formic acid, chloracetic acid, and cyanoacetic acid. Analyses of the kinetic data including the Bronsted plots have shown that the reaction is subject to a general acid catalysis.
A novel synthesis of isothiocyanates from amines and phenyl isothiocyanate via replacement reaction
Zhu, Shou-ji,Li, Jin-feng
, p. 4543 - 4547 (2021)
A new efficient method for the synthesis of isothiocyanates has been developed via the replacement reaction of phenyl isothiocyanate and the corresponding amines (the amino group of these amines was linked to tertiary carbon or secondary carbon) with dimethylbenzene as solvent. This reaction was carried out under the protection of nitrogen and mild condition. In addition, the yields of some products could be more than 90%. More importantly, this method has advantages with low toxicity, low cost, safety, less by-products and simple to operate. It has the potential to realize the industrial production of some complicated isothiocyanates.
New 2-Aminothiazoline derivatives lower blood pressure of spontaneously hypertensive rats (SHR) via I1-imidazoline and alpha-2 adrenergic receptors activation
Ferreira, Renan B.,de Oliveira, Mariana G.,Antunes, Edson,Almeida, Wanda P.,Ibrahim, Badr M.,Abdel-Rahman, Abdel A.
, p. 803 - 810 (2016)
2-Aminothiazolines share an isosteric relationship with imidazolines and oxazolines with antihypertensive activity mainly mediated by the imidazoline I1-receptor. In the present work, we have prepared five aminothiazolines, following a previously described synthetic pathway. Aminothiazolines derived from dicyclopropylmethylamine (ATZ1) and cyclohexylamine (3) are unprecedented in the literature. Competitive radioligand assay was carried out with all synthetic compounds, and the I1receptor affinity in comparison to rilmenidine in PC12 cells was determined. Surprisingly, the rilmenidine isoster (ATZ1) showed no I1-receptor interaction. Diethyl (ATZ4) and 2-ethyl-hexylamine (ATZ5) derivatives bind to the receptor with 11.98 and 10.94 nmol/l, respectively. These compounds were selected for in vivo experiments. Both compounds reduced the blood pressure of spontaneously hypertensive rats (SHR). The hypotensive effect of these compounds was abrogated in the presence of α2adrenergic (yohimbine) and I1(efaroxan) receptor antagonists suggesting that both aminothiazolines bind to the adrenergic and imidazoline receptors. Lipinski's descriptors of the synthesized aminothiazolines were calculated and are similar to the known imidazoline I1receptor ligands. 3D-Similarity between ATZ5 and agmatine, the natural imidazoline receptor ligand, was also observed.
4-Dimethylaminopyridine-catalyzed synthesis of isothiocyanates from amines and carbon disulfide
Rong, Hao-Jie,Chen, Tao,Xu, Ze-Gang,Su, Tian-Duo,Shang, Yu,Wang, Yong-Qiang,Yang, Cui-Feng
, (2021)
Isothiocyanates were synthesized by reactions between primary amines and CS2 in the presence of 4-dimethylaminopyridine as a catalyst and tert-butyl hydroperoxide as an oxidant. Various aryl, benzyl, alkyl, and hydroxyl amines were transformed into the corresponding isothiocyanates in 41–82% yields.
A marvelous catalysis of tellurium in the formation of isothiocyanates from isocyanides and sulfur
Fujiwara, Shin-Ichi,Shin-Ike, Tsutomu,Okada, Kazuhiro,Aoki, Minoru,Kambe, Nobuaki,Sonoda, Noboru
, p. 7021 - 7024 (1992)
Catalytic activity of tellurium in the formation of isothiocyanates from isocyanides and sulfur has been found to be extremely high and far superior to that of selenium.
Efficient conversion of thiols to thiocyanates by in situ generated Ph3P(SCN)2
Iranpoor, Nasser,Firouzabadi, Habib,Shaterian, Hamid Reza
, p. 3439 - 3441 (2002)
A new, novel, rapid and simple method is described for the one-pot conversion of thiols to thiocyanates by use of in situ generated PPh3(SCN)2 at room temperature.
Diaryl-substituted thiosemicarbazone: A potent scaffold for the development of New Delhi metallo-β-lactamase-1 inhibitors
Li, Jia-Qi,Sun, Le-Yun,Jiang, Zhihui,Chen, Cheng,Gao, Han,Chigan, Jia-Zhu,Ding, Huan-Huan,Yang, Ke-Wu
, (2020/12/30)
The superbug infection caused by New Delhi metallo-β-lactamase (NDM-1) has become an emerging public health threat. Inhibition of NDM-1 has proven challenging due to its shuttling between pathogenic bacteria. A potent scaffold, diaryl-substituted thiosemicarbazone, was constructed and assayed with metallo-β-lactamases (MβLs). The obtained twenty-six molecules specifically inhibited NDM-1 with IC50 0.038–34.7 μM range (except 1e, 2e, and 3d), and 1c is the most potent inhibitor (IC50 = 0.038 μM). The structure-activity relationship of synthetic thiosemicarbazones revealed that the diaryl-substitutes, specifically 2-pyridine and 2-hydroxylbenzene improved inhibitory activities of the inhibitors. The thiosemicarbazones exhibited synergistic antimycobacterial actions against E. coli-NDM-1, resulted a 2–512-fold reduction in MIC of meropenem, while 1c restored 16–256-, 16-, and 2-fold activity of the antibiotic on clinical isolates ECs, K. pneumonia and P. aeruginosa harboring NDM-1, respectively. Also, mice experiments showed that 1c had a synergistic antibacterial ability with meropenem, reduced the bacterial load clinical isolate EC08 in the spleen and liver. This work provided a highly promising scaffold for the development of NDM-1 inhibitors.
A more sustainable isothiocyanate synthesis by amine catalyzed sulfurization of isocyanides with elemental sulfur
Nickisch,Conen,Gabrielsen,Meier
, p. 3134 - 3142 (2021/01/28)
Isothiocyanates (ITCs) are typically prepared using amines and highly toxic reagents such as thiophosgene, its derivatives, or CS2. In this work, an investigation of a multicomponent reaction (MCR) using isocyanides, elemental sulfur and amines revealed that isocyanides can be converted to isothiocyanates using sulfur and catalytic amounts of amine bases, especially DBU (down to 2 mol%). This new catalytic reaction was optimized in terms of sustainability, especially considering benign solvents such as Cyrene or γ-butyrolactone (GBL) under moderate heating (40 °C). Purification by column chromatography was further optimized to generate less waste by maintaining high purity of the product. Thus, E-factors as low as 0.989 were achieved and the versatility of this straightforward procedure was shown by converting 20 different isocyanides under catalytic conditions, while obtaining moderate to high yields (34-95%). This journal is
