118090-09-8Relevant articles and documents
Studies and X-ray determinations with 2-(acetonylthio)benzothiazole: Synthesis of 2-(benzothiazol-2-ylthio)-1-phenylethanone and 2-(acetonylthio) benzothiazole by C - S bond cleavage of 2-(acetonylthio)benzothiazole in KOH
Al-Omran, Fatima,El-Khair, Adel Abou
, p. 62 - 70 (2014)
New route for the synthesis of 2-(benzothiazol-2-ylthio)-1-phenylethanone (6) and 2-(acetonylthio)benzothiazole (1) by using phenacyl bromide and α-chloroacetone, respectively, through carbon-sulfur bond cleavage reactions in a basic medium has been generated. Treatment of 1 with malononitrile and elemental sulfur afforded the corresponding derivative of 2-amino-3-cyanothiophene (12), whereas treatment of 1 with cyanoacetohydrazide afforded the corresponding derivative of cyanoacetylhydrazone derivative (13). The structure of the synthesis compounds has been established on the basis of elemental analyses, 1H-NMR, 13C-NMR, correlation spectroscopy, heteronuclear single quantum coherence, MS spectra, and X-ray crystallographic investigations.
Synthesis, in vitro α-glucosidase inhibitory activity and molecular docking studies of novel benzothiazole-triazole derivatives
Gong, Zipeng,Peng, Yaping,Qiu, Jie,Cao, Anbai,Wang, Guangcheng,Peng, Zhiyun
, (2017)
Benzothiazole-triazole derivatives 6a–6s have been synthesized and characterized by1H-NMR and13C-NMR. All synthetic compounds were screened for their in vitro α-glucosidase inhibitory activity by using Baker’s yeast α-glucosidase enzyme. The majority of compounds exhibited a varying degree of α-glucosidase inhibitory activity with IC50 values between 20.7 and 61.1 μM when compared with standard acarbose (IC50 = 817.38 μM). Among the series, compound 6s (IC50 = 20.7 μM) bearing a chlorine group at the 5-position of the benzothiazole ring and a tert-butyl group at the para position of the phenyl ring, was found to be the most active compound. Preliminary structure-activity relationships were established. Molecular docking studies were performed to predict the binding interaction of the compounds in the binding pocket of the enzyme.
Liquid chromatography/mass spectrometry identification of intermediates and vulcanization products by using squalene as vulcanization model compound
Giansanti, Luisa,Aleandri, Simone,Altieri, Barbara,Caretti, Fulvia,Mancini, Giovanna,Morosetti, Stefano,Ventura, Salvatore,Pérez-Fernández, Virginia,Gentili, Alessandra
, p. 1339 - 1348 (2016)
Rationale Sulfur-vulcanized rubber is a three-dimensional polymer network, insoluble in all organic solvents. For this reason, vulcanization products are difficult to study and identify by conventional analytical techniques. To simplify this task, low molecular weight olefins have been used as model compounds (MCs) in place of rubber in vulcanization experiments. Methods In this work, the vulcanization process was investigated using squalene (SQ) as MC. By-products, intermediates and products were separated by semipreparative reversed-phase liquid chromatography (RPLC) with UV detection. Each fraction was collected, concentrated and characterized by flow injection analysis (FIA) and non-aqueous reversed-phase (NARP) LC coupled to positive atmospheric pressure chemical ionization mass spectrometry (APCI-MS). Under the latter conditions, an Information-Dependent Acquisition (IDA) was performed on a linear ion trap mass spectrometer to obtain structural information. Results Several vulcanized compounds containing up to three SQ molecules, cross-linked with chains involving up to 14 sulfur atoms overall, have been identified along with some of their oxidized products (epoxides and hydroperoxides). The FIA-MS spectra showed peak clusters, each of which included two-three subclusters; the interpretation was complicated by the occurrence of more ion species per product, by the unsaturation grade and by the characteristic isotopic distribution of sulfur. The enhanced product ion scan (EPI) spectra, acquired during the IDA experiments, supported the FIA-MS identification allowing one to count the number of sulfur atoms. Conclusions The sensitivity of the developed analytical strategy was due to the enrichment factor achieved via semipreparative chromatography and the very good response of the APCI detection. Pattern fragmentation and chromatographic behavior simplified the identification of the cured compounds and their oxidized products, whose occurrence was related to the grade of oxidation of SQ used as reagent.
Metal sulfide: An efficient promoter for the synthesis of 2-mercaptobenzothiazoles from 2-haloanilines and carbon disulfide
Zhang, Tianmiao,Qin, Weijing,Zhu, Ning,Han, Limin,Wang, Liubo,Hong, Hailong
, p. 1916 - 1925 (2017)
A convenient method has been developed for the preparation of a variety of 2-mercaptobenzothiazoles from 2-haloanilines and CS2 mediated by metal sulfide. In this reaction, 2-haloanilines reacted with CS2 in the presence of Na2S · 9H2O to form 2-mercaptobenzothiazoles. Na2S · 9H2O functioned both as an activator of CS2 and as a base. Furthermore, NMR analysis was used to identify the different reaction mechanisms of 2-haloanilines and CS2 mediated by Na2S or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), which demonstrated that Na2S interacted only with CS2, while DBU reacted with both 2-iodoaniline and CS2.
Coordination modes of 2-mercapto-1,3-benzothiazolate in gallium and indium complexes
Basiak, Dariusz,Ziemkowska, Wanda,Socha, Pawe?,Dobrzycki, ?ukasz,Ochal, Zbigniew,Pindelska, Edyta
, p. 1528 - 1535 (2017)
2-Mercapto-1,3-benzothiazole (mbztH) may act as a chelating or bridging ligand. In this study, reactions of mbztH with Me3Ga and Me3In were examined. The products were characterized by NMR spectroscopy, elemental analyses, melting point, and molecular weight determinations. Formation of mononuclear chelating complexes Me2M(mbzt) (M?=?Ga, In) was observed in solutions. Crystallization of Me2M(mbzt) yielded uncommon non-symmetrical dinuclear complexes Me4M2(mbzt)2, in which one metal is bonded to two sulfurs and the other to two nitrogens.
An efficient copper-catalyzed synthesis of 2-mercaptobenzothiazole through S-arylation/heterocyclization of 2-haloaniline with potassium xanthate
Liu, Lei,Zhu, Ning,Gao, Min,Zhao, Xiaole,Han, Limin,Hong, Hailong
, p. 699 - 701 (2016)
A mild and efficient methodology to produce 2-mercaptobenzothiazoles in DMF via ortho-haloaniline coupling with potassium O-ethyl dithiocarbonate catalyzed by copper without a ligand has been developed.
A modified procedure for synthesis of the side chain of ceftazidime-activated thioester
Li, Lei,Wang, Guangyuan,Wei, Shanshan,Yan, Xilong,Chen, Ligong
, p. 615 - 620 (2013)
A modified procedure for synthesis of the side chain of ceftazidime-activated thioester has been established. This key intermediate of ceftazidime was obtained by a more eco-friendly process than conventional methods, and the yield was much higher (up to
CARBON-CARBON BOND FORMATION VIA PHOSPHINE-INITIATED CLEAVAGE OF β-OXOSULFIDES
Ueno, Yoshio,Yadav, L. D. S.,Okawara, Makoto
, p. 831 - 834 (1983)
2-(Phenacylthio)benzothiazole (1) reacted with aldehyde or ketone in the presence of tri-n-butylphosphine at 80 deg C to give α,β-enone and 2-mercaptobenzothiazole in good yield.The reaction scheme for this new type of enolate ion formation via C-S bond cleavage is also described.
Efficient, Iron-Catalyzed Synthesis of 2-Mercaptobenzothiazole Through S-Arylation/Heterocyclization of 2-Haloaniline with Potassium Xanthate
Gao, Min,Lou, Chunqing,Zhu, Ning,Qin, Weijing,Suo, Quanling,Han, Limin,Hong, Hailong
, p. 2378 - 2385 (2015)
A mild and practical method for the synthesis of 2-mercaptobenzothiazole has been developed by using iron as an efficient catalyst. The present tandem reaction process allows access to a wide range of 2-mercaptobenzothiazoles in good to excellent yields by the reaction of 2-haloaniline with potassium O-ethyl dithiocarbonate in the presence of FeF3 as a catalyst and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl as a ligand under an atmosphere of argon.
A chemical looping technology for the synthesis of 2,2′-dibenzothiazole disulfide
Tian, Jiaxin,Jiayu Hu,Wang, Kai,Deng, Jian,Luo, Guangsheng
, p. 2778 - 2785 (2020)
A novel chemical looping technology for the synthesis of 2,2′-dibenzothiazole disulfide (MBTS) with zero emissions has been developed. Through chemical cycling between carbonate and bicarbonate in the reaction system, the insoluble 2-mercaptobenzothiazole (MBT) can become soluble in the aqueous phase of sodium carbonate and then be oxidized efficiently by hydrogen peroxide and the absorption of CO2 with high selectivity. The mother liquor can be totally recycled by the desorption of CO2 without any generation of salt-containing wastewater. With the new synthesis technology, the product has high purity and reaches the standard of a superior product that can be applied as a vulcanization accelerator. When 5.0 wt% hydrogen peroxide was added dropwise over 40 min at 50 °C, the conversion ratio of MBT was over 98%. The mother liquor was recycled 5 times and no side-products were found. The whole process is clean and pollution-free, which greatly reduces the burden of hazardous waste treatment and brings great environmental benefits.
