- Cleaner and greener synthesis of 3H-benzothiazole-2-thione and its derivatives
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A cleaner and greener method of synthesis of 3H-benzothiazole-2-thione is being reported in this communication. In this method, various o-iodoaniline derivatives are reacted with carbon disulfide in the presence of Cs2CO3 and tetramethyl ammonium bromide (TMAB) to give 3H-benzothiazole-2-thione and its derivatives in higher yields.
- Srivastava, Nitin,Kishore, Ram
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- Water-Promoted Chlorination of 2-Mercaptobenzothiazoles
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Substituted benzothiazoles play an important role in medicinal chemistry due to their pharmacological properties. Their 2-substituted derivatives are often prepared from 2-chlorobenzothiazoles, which in turn can be synthesized from the 2-mercapto precursor using sulfuryl chloride. In practice, this seemingly straightforward and widely used reaction can be impeded by poor reproducibility and low reaction yields. In this communication, we report that the simple addition of water to the reaction leads to remarkable improvements in reaction efficiency. We attribute this effect to the formation of acid through partial hydrolysis of sulfuryl chloride. This hypothesis is supported by the observation that improved yields were also obtained in the presence of some anhydrous acidic additives. The simple combination of sulfuryl chloride and water reproducibly provides excellent yields for a range of chlorinated products.
- Wimmer, Laurin,Parmentier, Michael,Riss, Bernard,Kapferer, Tobias,Ye, Chao,Li, Lei,Kim, Hongyong,Li, Jialiang
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p. 2027 - 2032
(2018/04/16)
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- Highly efficient synthesis of 2-mercaptobenzothiazole derivatives in water: Metal sulfide-disulfide dynamic interchange reaction
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A convenient and efficient method for the synthesis of 2-mercaptobenzothiazoles from disulfide and CS2 mediated by a metal sulfide in water is described. This synthetic methodology could be used to prepare diverse 2-mercaptobenzothiazole derivatives in good to excellent yields. In this paper, the concept of metal sulfide-disulfide dynamic interchange reaction was put forward. Then the intermediates of the interchange reaction between NaHS and a disulfide were detected by LC-MS, which demonstrated that the S-S bond of the disulfide could be broken by the metal sulfide through the dynamic interchange reaction. In addition, NaHS was eventually transformed into sulfur S8 by the dynamic interchange reaction. Moreover, the underlying mechanism of 2-mercaptobenzothiazole formation is proposed, in which NaHS not only acts as an S-S bond cleaving agent but also as an activator of CS2. As a result, a novel synthetic route for the preparation of sulfur-containing heterocycles from a disulfide is developed.
- Lou, Chunqing,Zhu, Ning,Fan, Ronghua,Hong, Hailong,Han, Limin,Zhang, Jianbin,Suo, Quanling
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p. 1102 - 1108
(2017/08/15)
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- Metal sulfide: An efficient promoter for the synthesis of 2-mercaptobenzothiazoles from 2-haloanilines and carbon disulfide
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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.
- Zhang, Tianmiao,Qin, Weijing,Zhu, Ning,Han, Limin,Wang, Liubo,Hong, Hailong
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supporting information
p. 1916 - 1925
(2017/09/27)
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- An efficient copper-catalyzed synthesis of 2-mercaptobenzothiazole through S-arylation/heterocyclization of 2-haloaniline with potassium xanthate
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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.
- Liu, Lei,Zhu, Ning,Gao, Min,Zhao, Xiaole,Han, Limin,Hong, Hailong
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p. 699 - 701
(2016/05/09)
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- Inorganic metal sulfide neighbouring halogen promoting the reaction of aniline with carbon disulfide synthesis of 2-mercaptobenzothiazole method
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The invention provides a method for synthesizing a 2-mercaptobenzothiazole derivate by utilizing 2-halogen phenylamine, carbon disulfide and inorganic metal sulfide as raw materials and relates to the field of medicines, industry and agriculture and the like. The synthesizing method comprises the steps of dissolving 2-halogen phenylamine and inorganic metal sulfide in an appropriate solvent, adding carbon disulfide to react for a certain time under the conditions of 90-130 DEG C, and performing purification treatment to obtain the product. The 2-mercaptobenzothiazole derivate can be synthesized rapidly and efficiently through the method, the raw materials used for the method are non-toxic, cheap and free of pollution, reaction conditions are moderate, aftertreatment is simple, and the yield is high.
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Paragraph 0047-0048
(2017/03/17)
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- Copper-Catalyzed Three-Component Synthesis of Benzothiazolethiones from o-Iodoanilines, Isocyanide, and Potassium Sulfide
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An efficient copper catalyzed strategy for the synthesis of a variety of benzothiazolethione derivatives has been developed. In the presence of CuCl, the three-component reaction of o-iodoanilines and K2S with p-toluenesulfonylmethyl isocyanide proceeded smoothly to obtain the corresponding benzothiazolethiones in good to excellent isolated yields. Notably, isocyanide functioned as a carbon source and K2S functioned as a sulfur source in this reaction.
- Dang, Pan,Zeng, Weilan,Liang, Yun
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supporting information
p. 34 - 37
(2015/07/28)
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- Efficient, Iron-Catalyzed Synthesis of 2-Mercaptobenzothiazole Through S-Arylation/Heterocyclization of 2-Haloaniline with Potassium Xanthate
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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.
- Gao, Min,Lou, Chunqing,Zhu, Ning,Qin, Weijing,Suo, Quanling,Han, Limin,Hong, Hailong
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supporting information
p. 2378 - 2385
(2015/10/12)
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- A convenient metal-free method for the synthesis of benzothiazolethiones from o-haloanilines and carbon disulfide
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A convenient method has been developed for the preparation of a variety of 1,3-benzothiazole-2(3H)-thiones. The reaction proceeds from an o-haloaniline derivative and carbon disulfide in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene at 80-140 °C to g
- Wang, Fei,Xi, Chanjuan,Zhao, Peng
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p. 1477 - 1480
(2020/01/03)
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- Synthesis of 2-mercaptobenzothiazoles via DBU-promoted tandem reaction of o-haloanilines and carbon disulfide
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An efficient strategy for the synthesis of a variety of 2-mercaptobenzothiazole derivatives has been developed. The reaction proceeded from o-haloaniline derivatives and carbon disulfide via a tandem reaction in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to afford the corresponding 2-mercaptobenzothiazole derivatives in good to excellent yields.
- Wang, Fei,Cai, Shangjun,Wang, Zhipeng,Xi, Chanjuan
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supporting information; experimental part
p. 3202 - 3205
(2011/08/07)
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- Synthesis and biological evaluation of 2-mercapto-1,3-benzothiazole derivatives with potential antimicrobial activity
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The enhancement of bacterial resistance of pathogens to currently available antibiotics constitutes a serious public health threat. So, intensive efforts are underway worldwide to develop new antimicrobial agents. To identify compounds with a potent antimicrobial profile, we designed and synthesized low molecular weight 2-mercaptobenzothiazole derivatives 2a-2l and 3a-3l. Both series were screened for in-vitro antibacterial activity against the representative panel of Gram-positive and Gram-negative bacteria strains. The biological screening identified compounds 2e and 2l as the most active ones showing an interesting antibacterial activity with MIC values of 3.12 μg/mL against Staphylococcus aureus and 25 μg/mL against Escherichia coli, respectively. The replacement of the S-H by the S-Bn moiety resulted in considerable loss of the antibacterial action of the 3a-3l series. The antibiotic action of compounds 2e and 2l was also investigated by testing their activity against some clinical isolates with different antimicrobial resistance profile. Moreover, the involvement of the NorA efflux pump in the antibacterial activity of our molecules was evaluated. Finally, in this paper, we also describe the cytotoxic activity of the most interesting compounds by MTS assay against HeLa and MRC-5 cell lines.
- Franchini, Carlo,Muraglia, Marilena,Corbo, Filomena,Florio, Marco Antonio,Di Mola, Antonia,Rosato, Antonio,Matucci, Rosanna,Nesi, Marta,Van Bambeke, Francoise,Vitali, Cesare
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experimental part
p. 605 - 613
(2009/12/26)
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- Synthesis, antioxidant properties and radioprotective effects of new benzothiazoles and thiadiazoles
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In this work, we report the synthesis and characterization of new compounds derived from benzothiazoles and thiadiazoles. We observed that structural modifications on these skeletons affected the antioxidant activity. Thiol and aminothiol compounds derived from thiadiazoles and benzothiazoles showed an interesting antioxidant property. The radioprotective activity has also been evaluated in mice. Some of these compounds could be good radioprotectors.
- Cressier, Damien,Prouillac, Caroline,Hernandez, Pierre,Amourette, Christine,Diserbo, Michel,Lion, Claude,Rima, Ghassoub
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experimental part
p. 5275 - 5284
(2009/12/04)
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- Convenient strategies for the preparation of modified 2(3H)-benzothiazolethiones
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4-Alkyl-2-bromoanilines and 4-alkoxy-2-chloroanilines were synthesized conveniently and submitted to cyclization reaction with potassium O-ethyl dithiocarbonate to afford 6-substituted 2(3H)-benzothiazolethiones in good yields.
- Chaudhuri, Narayan C.
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p. 3783 - 3790
(2007/10/03)
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- 3-thioheteroaryl 1-carba-1-dethiacephalosporin compounds, compositions and methods of use
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1-Carba-1-dethiacephalosporin compounds of the formula I STR1 are disclosed. The compounds are useful against MRSA/MRCNS. Compositions and methods of use are also included.
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- Heterocyclic compounds
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The invention provides compounds of formula (I) having nematicidal, insecticidal, acaricidal and fungicidal properties, compositions comprising them and processes and intermediates for their preparation: STR1 wherein: X is oxygen or sulphur; n is 0, 1 or 2; R1, R2, R3, and R4 are as described in the specification.
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- Process for the preparation of 2-mercaptobenzothiazoles
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The preparation of (optionally substituted) 2-mercaptobenzothiazole by reaction of corresponding 2-halogenoanilines with an alkali metal xanthate or alkaline earth metal xanthate or with CS2 in the presence of bases.
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