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Visible light promoted synthesis of N-aroylsulfoximines by oxidative C–H acylation of NH-sulfoximines

Science China Chemistry 2019年第9期62卷 1213-1220页

作者： Wenlong Jiang Youming Huang Lihong Zhou Qingle Zeng State Key Laboratory of Geohazard Prevention and Geoenvironment Protection College of Materials Chemistry & Chemical Engineering Chengdu University of Technology Chengdu 610059 China College of Environment and Ecology Chengdu University of Technology Chengdu 610059 China

The visible light-promoted synthesis of N-aroylsulfoximines has been accomplished via an oxidative dehydrogenative coupling at room temperature under air without the addition of a photosensitizer, metal catalyst, or base. This process exhibits good functional group tolerance, allows facile isolation and purification, and affords N-aroylsulfoximines with high efficiency. The efficiency of the newly developed protocol is described in detail with 27 examples with yields ranging from 80% to 96%.Furthermore, the chirality of the NH-sulfoximine is completely maintained in the desired N-aroylsulfoximine product(>99% ee).

关键词： visible light aldehyde sulfoximines acylation oxidative dehydrogenative coupling

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Design, Synthesis, Biological Evaluation and SARs of Novel N-Substituted Sulfoximfnes as Potential Ryanodine Receptor Modulators

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Chinese Journal of Chemistry 2018年第2期36卷 129-133页

作者： Yongtao Xie Sha Zhou Yuxin Li Shaa Zhou Minggui Chen Baolei Wang Lixia Xiong Na Yang Zhengming Li State Key Laboratory of Elemento-Organic Chemistry Department of Chemistry Collaborative innovation Center of Chemical Science and Engineering Nankai University Tianjin 300071 China

The sulfoximine group has been evaluated as a pharmacophore. Introducing the sulfoximine structure into medicinal compounds as exciting motifs has brought opportunities in drug discovery. In order to develop new ryanodine receptor （RyR） modulators, a series of phthalamides containing sulfoximine derivatives were designed, synthesized, and evaluated against oriental armyworm and diamondback moth for their insecticidal activities. These studies helped to elucidate the electronic and structural requirements around the sulfoximine motif for insecticidal activity. All new structures were synthesized and characterized by ^1H NMR, ^13C NMR, HRMS and bioassay and a preliminary structure-activity relationship （SAR） was discussed. The biological assessment indicated that most title compounds showed good to excellent larvicidal activities. Compounds la, le, and If gave excellent insecticidal activity against oriental armyworm, which showed 100% larvicidal activity at 0.5 mg/L. All compounds showed 100% larvicidal activity at 0.1 mg/L against diamondback moth. In particular, the larvicidal activities of le, If, and lh at 0.0001 mg/L were 50%, 20%, and 40%, respectively, reaching an activity as high as that of the commercial flubendiamide （40%, 0.0001mg/L）. Therefore, Ia, Ie, If and Ih could be considered as new lead structures for the development of new ryanodine receptor （RyR） modulators.

关键词： sulfoximines SAR insecticidal activity ryanodine receptor

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Strain-promoted S-arylation and alkenylation of sulfinamides using arynes and cyclic alkynes

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Science China Chemistry 2024年第3期67卷 928-935页

作者： Xi Zou Boming Shen Gao-lin Li Qian Liang Yanhua Ouyang Binghe Yang Peiyuan Yu Bing Gao State Key Laboratory of Chemo/Bio-Sensing and Chemometrics College of Chemistry and Chemical EngineeringInstitute of Chemical Biology and NanomedicineHunan UniversityChangsha 410082China Department of Chemistry and Shenzhen Grubbs Institute Guangdong Provincial Key Laboratory of CatalysisSouthern University of Science and TechnologyShenzhen 518055China

The conversion of commercially available chiral sulfinamides into pharmaceutically useful chiral sulfoximines via direct SIVfunctionalization is synthetically attractive but challenging due to the competitive reaction of N-functionalization. Herein, we disclose a novel strain-release strategy to access stereospecific and chemoselective SIV-arylation and alkenylation of sulfinamides using arynes and strained cyclic alkynes. This method tolerates an unprecedented chemical diversity of functional groups attached to the nitrogen center(N-R). The origin of the high SIV-selectivity is elucidated by density functional theory calculations, suggesting a stepwise mechanism for the aryne substrates and a concerted mechanism for the cyclic alkynes.

关键词： arylation alkenylation sulfoximines sulfinamides arynes

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Design, Synthesis, Structure-Activity Relationship and Insecticidal Activities of Trifluoromethyl-Containing Sulfiliminyl and Sulfoximinyl Phthalic Acid Diamide Structure

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Chinese Journal of Chemistry 2014年第7期32卷 567-572页

作者： Sha Zhou Tao Yan Sha Zhou Xuewen Hua Baolei Wang Yucheng Gu Lixia Xiong Yongqiang Li Zhengming Li State Key Laboratory of Elemento-Organic Chemistry Collaborative Innovation Center of Chemical Science and Engineering(Tianjin)Nankai UniversityTianjin 300071China School of Mechanical Engineering Tianjin Polytechnic UniversityTianjin 300071China Syngenta Jealott’s Hill International Research Centre BracknellBerkshireRG426EYUK

Due to a novel mode action,low toxicity to mammals and low residue characteristics,phthalic acid diamides have aroused considerable interests in agricultural *** introduction of N-cyano,N-trifluoroacetyl,N-carbamoylsulfiliminyl and sulfoximinyl substituents into phthalamides,12 novel derivatives containing trifluoromethyl moiety were designed and *** title compounds were characterized by ^(1)H NMR and high-resolution mass *** preliminary results of biological activity assessment indicated that some title compounds exhibited moderate to good insecticidal activities against oriental armyworm(Pseudaletia separata Walker).In particular,Va gave higher activity against oriental armyworm and diamondback *** present work reported that the new trifluoromethylated diamides incorporating N-trifluoroacetylsulfoximinyl moieties are potential lead compounds for further structure optimization,providing some insight into the relating structure-activity relationship.

关键词： insecticidal activity ryanodine receptor sulfilimines sulfoximines trifluoromethylated

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