- Metal-free synthesis of 2-mercaptobenzothiazoles and 6-(4-substituted-1H-1,2,3-triazol-1-yl)-2-mercaptobenzothiazoles via microwave-assisted synthesis pathway
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A simple, efficient, and metal-free methodology for the preparation of 2-mercaptobenzothiazole and derivatives in excellent yields via microwave-assisted pathway is reported. Our condition provides a convenient protocol for the synthesis of a diverse collection of 2-mercaptobenzothiazoles and 6-(4-substituted-1H-1,2,3-triazol-1-yl)-2-mercaptobenzothiazoles with a very simple purification process. This report provides an alternative protocol for fast access to the wide range of compounds for sequence synthesis and biological studies.
- Tung, Truong Thanh,Huy, Luong Xuan
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supporting information
p. 2007 - 2014
(2020/05/29)
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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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- Rapid Access to a Broad Range of 6′-Substituted Firefly Luciferin Analogues Reveals Surprising Emitters and Inhibitors
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Light-emitting firefly luciferin analogues contain electron-donating groups in the 6′-position, but the scope of known 6′-substitution remains narrow. A two-step route to a broad range of 6′-substituted luciferin analogues was developed to fill this void and enable more extensive study of the 6′-functionality. This chemistry allowed direct access to "caged" amide and bright azetidine analogues, but also revealed thioether inhibitors and unexpectedly luminogenic aryl amine derivatives.
- Sharma, Deepak K.,Adams, Spencer T.,Liebmann, Kate L.,Miller, Stephen C.
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supporting information
p. 5836 - 5839
(2017/11/10)
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- General Entry into o-,o′-Heteroatom-Linked N-(Hetero)aryl-Imidazole Motifs by Gold-Catalysed Formal [3+2]-Dipolar Cycloaddition
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A general redox-neutral approach into the o-,o′-heteroatom-linked N-(hetero)aryl-imidazole family of heteroaromatics has been developed. New types of heteroatom substituted carbimidoyl nitrenoids are efficiently realised from robust, bench-stable N-(heteroaryl)-pyridinium-N-aminides by formal gold-catalysed [3+2]-dipolar cycloadditions across ynamides. Broad structural variety and functional group tolerance allows rapid access into diverse functionalised scaffolds, as exemplified by the preparation of 8 different heteroaromatic cores. (Figure presented.).
- Garzón, Miguel,Arce, Elsa M.,Reddy, Raju Jannapu,Davies, Paul W.
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supporting information
p. 1837 - 1843
(2017/06/09)
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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 0040-0041
(2017/03/17)
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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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- 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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- PYRAZINE COMPOUNDS AS PHOSPHODIESTERASE 10 INHIBITORS
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Pyrazine compounds, and compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.
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Page/Page column 97
(2010/06/15)
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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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- Improved synthesis of 2-(3H)benzothiazolethiones under microwave irradiation
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2-(3H)Benzothiazolethiones (2-mercaptobenzothiazole) are prepared by an improved method, which utilizes microwave-assisted cyclization of the corresponding ortho-haloanlines with potassium O-ethyl dithiocarbonate. By using microwave irradiation, the relative reactivity of 2-chloroanilines was greatly improved to the same level as that of 2-fluoroanilines and 2-bromoanilines. Copyright Taylor & Francis Group, LLC.
- Huang, Wei,Tan, Ying,Ding, Ming-Wu,Yang, Guang-Fu
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p. 369 - 376
(2007/10/03)
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- A convenient synthesis of 2-mercapto and 2-chlorobenzothiazoles
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A convenient synthesis of 2-mercapto and 2-chlorobenzothiazoles is described. The key feature of the synthesis is an exclusive ortho-selective nucleophilic aromatic substitution reaction of ortho-haloanilines with potassium/sodium O-ethyl dithiocarbonate under mild conditions. Subsequent intra-molecular cyclization affords 2-mercaptobenzothiazoles in high yields. The 2-mercaptobenzothiazoles are readily converted to corresponding 2-chlorobenzothiazoles upon treatment with sulfuryl chloride.
- Zhu, Lei,Zhang, Mingbao,Dai, Miao
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p. 727 - 730
(2007/10/03)
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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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