- Efficient Synthesis of Benzothiazolone Derivatives by a Domino Reaction of Disulfide and COS under Mild Conditions
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Carbonyl sulfide (COS), whose molecular structure is similar to CO2 and CS2, could be used as a better alternative carbonyl reagent due to its high chemical activity. However, the unfriendly by-product H2S would be generated when COS is used as a carbonyl reagent in the carbonylation reaction. In this report, the odorless and stable disulfide was used to replace the traditional foul smelling and unstable o-aminobenzenethiol to react with COS for preparing benzothiazolone derivatives in excellent yield, in which coupling reaction of H2S generation and S–S bond cleavage was firstly designed. Notably, the C=O of COS was converted into benzothiazolone derivatives by carbonylation reaction and the sulfur of COS was transformed into sulfur and sulfide after cleaving the S–S bond by a domino reaction of disulfide and COS under mild conditions. This efficient synthetic methodology provided a promising process for the utilization of COS.
- Zhou, Bohao,Hong, Hailong,Wang, Hongcai,Zhang, Tianmiao,Han, Limin,Zhu, Ning
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p. 6983 - 6990
(2019/01/04)
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- Method for synthesizing benzothiazole-2-ketone derivative from carbonyl sulfide and disulfide as raw materials
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The invention discloses a method for synthesizing a benzothiazole-2-ketone derivative from carbonyl sulfide and disulfide as raw materials. The method comprises the following steps: mixing disulfide,inorganic sulfide and an organic solvent, introducing sufficient COS to implement a reaction, and concentrating and purifying a reaction liquid, thereby obtaining the benzothiazole-2-ketone derivative. The inorganic sulfide used in the method is adopted as an activation catalyst and is low in price and easy to obtain; a catalysis system is relatively simple, and no other catalyst promoter is addedexcept reactants and inorganic sulfide; direct dehydration is implemented in the reaction process, no other dehydration agent is used, and thus the atom economy is improved; the catalysis system is good in applicability, is applicable to synthesis of fine chemicals with high additional values, and is very good in substrate applicability to each fine chemical with high additional values; reactionsare implemented at normal temperatures, normal pressure or low pressure, and thus danger coefficients can be reduced; the reaction time is short, and the efficiency can be improved.
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Paragraph 0043; 0044; 0045; 0069; 0070; 0071; 0072; 0074
(2018/06/26)
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- Method for synthesizing benzothiazolone-based and 1,3-disubstituted urea-based derivatives through activation of CO2
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The present invention relates to a method for synthesizing benzothiazolone-based and 1,3-disubstituted urea-based derivatives through activation of CO2. According to the present invention, an inexpensive and easily-available sulfur-containing metal salt compound is first used as an activation catalyst for CO2, and a reaction raw material and CO2 are converted into a corresponding target compound at a low reaction temperature under a low CO2 pressure; and the method has high atomic economy, can reduce the generation of by-products, meets the standards of environmental friendliness and environmentally friendly chemistry, and is the effective way capable of completely utilizing CO2 as the renewable resource, developing new energy and achieving the beneficial cycle of carbon in nature.
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Paragraph 0047; 0048; 0049; 0052; 0053
(2018/09/12)
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- Anti-diabetic activity of fused PPARγ-SIRT1 ligands with limited body-weight gain by mimicking calorie restriction and decreasing SGK1 expression
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A series of benzothiazol-2-one containing α-ethoxyphenylpropionic acid derivatives incorporating resveratrol or butein scaffolds were designed as fused full PPARγ agonist ligands and SIRT1-activating compounds for the treatment of type 2 diabetes (T2D) an
- Pirat, Celine,Dacquet, Catherine,Leclerc, Veronique,Hennuyer, Nathalie,Beucher-Gaudin, Monique,Zanirato, Ghislaine,Géant, Anne,Staels, Bart,Ktorza, Alain,Farce, Amaury,Caignard, Daniel-Henri,Berthelot, Pascal,Lebegue, Nicolas
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p. 310 - 326
(2017/06/14)
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- 6-Sulfonylbenzothiazolones as potential scaffolds for the design of 5-HT6 ligands
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5-HT6 Receptors are relatively recently discovered receptors that interact with cholinergic, glutamatergic, GABAergic and dopaminergic transmission systems. These receptors have been implicated in the CNS system as therapeutic targets in applications such as psychosis, reduction of body weight or Alzheimer's disease. As part of our efforts to develop 5-HT6 antagonists, we explored the benzothiazolone scaffold substituted in position 3 or 6 respectively with ethylamino chains and an aromatic ring connected through a sulfonyl linker. Final compounds were evaluated in radioligand binding assays for their ability to interact with 5-HT6 receptors. Their potential cytotoxic effects were determined on the human neuroblastoma cell line SY5Y. They showed very low cytotoxicity, and one of them has submicromolar affinity for 5-HT6 receptors.
- Larchanche, Paul-Emmanuel,Ultré, Vincent,Le Broc, Delphine,Ballandone, Céline,Furman, Christophe,Dallemagne, Patrick,Melnyk, Patricia,Carato, Pascal
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p. 807 - 817
(2015/03/05)
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- Synthesis and pharmacological evaluation of benzannulated derivatives as potent and selective sigma-1 protein ligands
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The σ1 proteins are considered to be a new class of target structures for several central nervous system disorders, including depression, anxiety, psychosis, and Parkinson's and Alzheimer's diseases. Recently, the involvement of these receptors
- Donnier-Maréchal, Marion,Carato, Pascal,Le Broc, Delphine,Furman, Christophe,Melnyk, Patricia
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p. 575 - 582
(2015/01/30)
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- Copper catalyzed three-component synthesis of benzothiazolones from o-iodoanilines, DMF, and potassium sulfide
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A copper catalyzed three-component reaction was developed for the synthesis of benzothiazolones. In the presence of CuBr2, the reaction of o-iodoanilines and K2S with DMF proceeded smoothly and generated the corresponding benzothiazolones with good isolated yields. DMF functioned both as the carbon monoxide source and as the reaction medium in this reaction.
- Yang, Yuan,Zhang, Xiaoyun,Zeng, Weilan,Huang, Hui,Liang, Yun
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p. 6090 - 6093
(2014/01/23)
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- Design and synthesis of 3-acyl-2(3H)-benzoxazolone and 3-acyl-2(3H)- benzothiazolone derivatives
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A simpler and efficient "green" method using solid sodium hydroxide in a solvent mixture of acetone/water was found to catalyze N-acylation of 2(3H)-benzoxazolones and 2(3H)-benzothiazolones for facile and rapid synthesis of N-acyl derivatives in excellent yields. This method was applied to the synthesis of a series of 132 compounds employing a variety of acyl chlorides. Graphical abstract: [Figure not available: see fulltext.]
- Guenadil, Faouzi,Aichaoui, Hocine,Kapanda, Coco N.,Lambert, Didier M.,McCurdy, Christopher R.,Poupaert, Jacques H.
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experimental part
p. 67 - 80
(2011/09/20)
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- Copper(I)-catalyzed cascade synthesis of 2-substituted 1,3-benzothiazoles: Direct access to benzothiazolones
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An efficient cascade process for the preparation of 2-substituted 1,3-benzothiazoles directly from 2-haloaryl isothiocyanates and O or S nucleophiles by a Cu-catalyzed, intramolecular, C-S bond formation has been developed. This cascade method is viable f
- Murru, Siva,Mondal, Pravat,Yella, Ramesh,Patel, Bhisma K.
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experimental part
p. 5406 - 5413
(2010/02/28)
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- Synthesis of 2-Oxo and 2-Thioxo-3(2H)-benzothiazoleethanimic Acid Anhydride with Acetic Acid and Related Products
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The reaction of the appropriate 2-benzothiazolinone with 2-chloroacetamide under basic conditions afforded the 2-oxo-3(2H)-benzothiazolineacetamides 6-9.The 2-thioxo-3(2H)-benzothiazolineacetamide (10) was prepared by the reaction of 3-(carbethoxymethyl)benzothiazoline-2-thione with ammonium hydroxide.The reaction of acetamides 6-10 with the appropriate anhydride containing a catalytic amount of the sodium salt of the acid corresponding to the anhydride afforded the titled compounds 11-18 in excellent yields.The omission of the catalyst in the same reaction furnished a mixture containing 57percent of the titled compound, 37percent of the nitrile and 6percent of an unknown.Possible mechanism and supporting nmr, ir and mass spectral data are discussed.
- D'Amico, John J.,Bollinger, Frederic G.,Freeman, John J.
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p. 1503 - 1509
(2007/10/02)
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