- 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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- Copper-Catalyzed One-Pot Synthesis of Chalcogen-Benzothiazoles/Imidazo[1,2- a ]pyridines with Sulfur/Selenium Powder and Aryl Boronic Acids
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An efficient and convenient copper-catalyzed oxidative chalcogenation of benzothiazoles and imidazo[1,2- a ]pyridines with sulfur/selenium powder and aryl boronic acids was developed. This procedure allows access to a wide range of structurally diverse arylchalcogen-substituted benzothiazoles/imidazo[1,2- a ]pyridines in good yields and with good functional group tolerance. A biological evaluation revealed that some of the obtained products exhibited in vitro antiproliferative activities on human-derived lung, stomach, esophageal, and breast cancer cell lines.
- Guo, Tao,Wei, Xu-Ning,Zhu, Ying-Li,Chen, Huan,Han, Shu-Lei,Ma, Yong-Cheng
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supporting information
p. 1530 - 1536
(2018/05/25)
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- Photo-induced copper-catalyzed C-H chalcogenation of azoles at room temperature
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Inexpensive copper catalysts enabled direct C-H chalcogenations at ambient temperature by means of photo-induced catalysis. The expedient copper catalysis set the stage for C-S and C-Se bond formation from readily accessible non-volatile elemental chalcogens. The photo-assisted copper catalysis manifold proved suitable for a wide range of substrates with good functional group tolerance and exhibited high catalytic efficacy even at a reaction temperature of 25 °C.
- Gandeepan, Parthasarathy,Mo, Jiayu,Ackermann, Lutz
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supporting information
p. 5906 - 5909
(2017/07/11)
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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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- Substrate-promoted ligand-free CuI catalyzed S-arylation of 2-mercaptobenzothiazoles with aryl iodides in water
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A green and efficient method has been developed for the cross-coupling of 2-mercaptobenzothiazoles with aryl iodides in water. The reactions proceeded smoothly under ligand-free conditions in the presence of TBAB to give the corresponding products in good yields. The protocol showed good tolerance toward a variety of functional groups. A substrate-promoted mechanism for this catalytic reaction has been proposed.
- He, Guozhen,Huang, Yuan,Tong, Yao,Zhang, Jie,Zhao, Dan,Zhou, Shuangli,Han, Shiqing
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supporting information
p. 5318 - 5321
(2013/09/12)
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- Intra- and Intermodular C-S bond formation using a single catalytic system: First direct access to arylthiobenzothiazoles
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We have for the first time developed two llgand-assisted Cu(I)-catalyzed sequential Intra- and intermolecular 5-arylations leading to the direct synthesis of arylthiobenzothlazoles In one pot without an Inert atmosphere. Low catalyst loading, inexpensive
- Murru, Siva,Ghosh, Harisadhan,Sahoo, Santosh K.,Patel, Bhisma K.
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supporting information; experimental part
p. 4254 - 4257
(2010/01/06)
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- Monosubstitution versus Disubstitution in the SRN1 Reaction of Dihalobenzenes with Sulfanions. The Role of the Monosubstitution Product and of Its Anion Radical
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The competition between mono- and disubstitution of dihalobenzenes by a series of aromatic sulfanions, via the SRN1 reaction, is shown to involve two radical chains.The first one, recognized in earliest works, involves one branching point at the level of the monosubstituted product anion radical.Reoxidation of the latter via electron transfer to the parent dihalide affords the monosubstituted product.Conversely, the route to the disubstituted product is opened when cleavage of the carbon-halogen bond in the monosubstituted product anion radical occurs before the electron transfer takes place; the disubstitution product is then obtained in its reduced (anion radical) form.Reoxidation of the latter, to afford the neutral disubstituted product, may involve competitively the parent dihalide or the neutral monosubstituted product, depending on the electron affinity of the arylthio moiety.In the first case the electron transfer propagates the first chain; in the second a new chain leading to the disubstitution is activated.The role of the two imbricated chains, under photochemical conditions, and thus that of the monosubstitution product is discussed quantitatively on the basis of the pertinent rate constants determined by cyclic voltammetry.
- Amatore, C.,Beugelmans, R.,Bois-Choussy, M.,Combellas, C.,Thiebault, A.
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p. 5688 - 5695
(2007/10/02)
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