- Copper(I)-Catalyzed Tandem One-Pot Synthesis of 2-Arylthiobenzothiazoles and 2-Arylthiobenzoxazoles in Water
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An efficient tandem process for the preparation of 2-arylthiobenzothiazoles has been developed. By condensation of 2-aminobenzenethiol with tetramethylthiuram disulfide (TMTD), 2-mercaptobenzothiazoles was in situ generated, which susequently underwent coupling with iodobenzenes to give the desired 2-arylthiobenzothiazoles fluently in a one-pot manner. This method can also be used for the synthesis of 2-arylthiobenzoxazoles. Inexpensive metal catalyst and ligand, mild reaction temperature, and water as solvent make this protocol practically valuable and useful in organic synthesis.
- Liu, Xing,Zhang, Shi-Bo,Zhu, Hui,Dong, Zhi-Bing
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p. 11703 - 11711
(2018/10/02)
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- New Synthesis and Biological Evaluation of Benzothiazole Derivates as Antifungal Agents
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In search of new antifungal agrochemicals that could replace commercially available, aryl-2-mercaptobenzothiazoles were synthesized. They were prepared by two methodologies, using both photostimulated reaction and microwave assisted reaction. These reactions took place without the use of metallic catalyst by a one-pot procedure with excellent yields (70-98%). Synthesized compounds were evaluated for fungal growth inhibition against Botrytis cinerea. Most of the compounds have an excellent antifungal activity, and three of these showed a superior inhibitory effect to commercial fungicide Triadimefon. IC50 values observed for 2-(phenylthio)benzothiazole, 2-(2-chlorophenylthio)benzothiazole, and 2-(3-chlorophenyl thio)benzothiazole were 0.75, 0.69, and 0.65 μg mL-1, respectively.
- Cano, Natividad Herrera,Ballari, María S.,López, Abel G.,Santiago, Ana N.
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p. 3681 - 3686
(2015/04/27)
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- Novel copper/PEG-400 catalyst systems for chemoselective S- and N-arylation of 2-mercaptobenzothiazole
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A novel approach for chemoselective S- and N-arylation of 2-mercaptobenzothiazole was developed by copper/PEG-400 catalyst systems. Copper source and reaction temperature play an important role in this protocol, selective S-arylation of 2-mercaptobenzothiazole was achieved by using CuI/PEG-400/50 °C catalyst system, while selective N-arylation was achieved with CuO/PEG-400/140 °C catalyst system. Both are compatible with a variety of aryl halides and selectively give the desired S- and N-arylation products in good to excellent yields, respectively.
- Li, Xiaokang,Yuan, Tangjun,Yang, Yu,Chen, Junmin
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supporting information
p. 9652 - 9660
(2015/01/09)
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- Copper oxide nanoparticle-catalyzed chalcogenation of the carbon-hydrogen bond in thiazoles: Synthesis of 2-(organochalcogen) thiazoles
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We present (homepage: www.ufsm.br) herein the application of copper nanoparticles/dio-rganyl dichalcogenides to promote the synthesis of 2-(organochalcogen)thiazoles via direct carbon-hydro-gen bond activation in thiazoles. A systematic study of the catalytic system revealed that the presence and amount of base played an essential role in this reaction. The results revealed that electron-donating and electron-withdrawing substituents, in the aromat-ic ring bonded to the chalcogen atom of diorganyl di-chalcogenides, required one equiv. of base, while when neutral substituents were present two equiv. of base were needed to deliver the products in similar yields.
- Rosario, Alisson R.,Casola, Kamila K.,Oliveira, Carla E.S.,Zeni, Gilson
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supporting information
p. 2960 - 2966
(2014/03/21)
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- The direct thiolation of benzothiazole catalyzed by copper complex in superbase system
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The copper-catalyzed direct thiolation of benzothiazole with iodobenzene and sulfur in superbase system under oxygen atmosphere is reported. The corresponding 2-thio-substituted benzothiazoles were formed in satisfactory yields. Georg Thieme Verlag KG Stu
- Wang, Xiaowei,Li, Yanjun,Yuan, Yu
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p. 1247 - 1255
(2013/06/04)
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- Iron-catalyzed S-arylation of thiols with aryl iodides
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(Chemical Equation Presented) Strike while the iron is hot: An efficient iron-catalyzed protocol for the S-arylation of aromatic and heteroaromatic thiol derivatives has been developed, which involves an inexpensive catalyst system formed by combining FeCl3 and N,N′-dimethylethylenediamine at 135°C. This method avoids the use of expensive and/or air-sensitive ligands and provides in most cases the desired sulfide in high yields.
- Correa, Arkaitz,Carril, Monica,Bolm, Carsten
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p. 2880 - 2883
(2008/12/23)
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