62266-82-4Relevant articles and documents
Method for synthesizing benzothiazole-2-ketone derivative from carbonyl sulfide and disulfide as raw materials
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Paragraph 0043; 0044; 0045; 0069; 0070; 0071; 0072; 0074, (2018/06/26)
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.
Efficient Synthesis of Benzothiazolone Derivatives by a Domino Reaction of Disulfide and COS under Mild Conditions
Zhou, Bohao,Hong, Hailong,Wang, Hongcai,Zhang, Tianmiao,Han, Limin,Zhu, Ning
, p. 6983 - 6990 (2019/01/04)
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.
6-Sulfonylbenzothiazolones as potential scaffolds for the design of 5-HT6 ligands
Larchanche, Paul-Emmanuel,Ultré, Vincent,Le Broc, Delphine,Ballandone, Céline,Furman, Christophe,Dallemagne, Patrick,Melnyk, Patricia,Carato, Pascal
, p. 807 - 817 (2015/03/05)
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.
