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Ru(Ⅲ)-catalyzed construction of variously substituted quinolines from 2-aminoaromatic aldehydes(ketones)and isoxazoles:isoxazoles as cyclization reagent and cyano sources

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Chinese Chemical Letters 2022年第8期33卷 4064-4068页

作者： Di Hu Chao Pi Wei Hu Xiliang Han Yangjie Wu Xiuling Cui Henan Key Laboratory of Chemical Biology and Organic Chemistry Key Laboratory of Applied Chemistry of Henan UniversitiesGreen Catalysis Center and College of ChemistryZhengzhou UniversityZhengzhou 450052China

A Ru(Ⅲ)-catalyzed annulation reaction of 2-aminoaromatic aldehydes(ketones)and isoxazoles to afford diverse 3-cyanoquinolines has been ***,isoxazole acted as a cyclization reagent and nontoxic cyano source via N-O bond cleavage and *** substituted(especially 6-or 7-substituted)quinolines could be easily *** procedure features wide functional group compatibility,efficiency and avoiding toxic cyano ***,this protocol could be successfully applied to scale-up *** chemical transformations of 3-cyanoquinoline could give some valuable skeletons,demonstrating its potential in synthetic application.

关键词： isoxazoles Cyclization reagent Cyano sources Variously substituted 3-cyanoquinolines

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Copper Nitrate-Mediated Selective Bond Cleavage of Alkynes:Diverse Synthesis of isoxazoles

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Chinese Journal of Chemistry 2023年第23期41卷 3299-3304页

作者： Jianan Liu Kaijing Zhou Shaobo Sun Mingchun Gao Bin Xu Department of Chemistry Affiliated Nantong Hospital of Shanghai University (The Sixth People's Hospital of Nantong)Shanghai Engineering Research Center of Organ RepairInnovative Drug Research CenterSchool of MedicineShanghai UniversityShanghai200444 China Qianweichang College Shanghai UniversityShanghai200444 China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai200032 China

An unprecedented copper nitrate-mediated bond cleavage of alkynes was developed for the modular synthesis of isoxazoles,where either C—S bond or C≡C triple bond was cleaved *** attached to the C≡C triple bonds could differentiate the chemical bonds cleavage and reaction pathways *** transformations of products illustrate promising applications of the given protocols.

关键词： Alkynes Bond cleavage Copper nitrate Cyclization isoxazoles Molecular diversity N-Heterocycles Substituent effects

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Synthesis of Trisubstituted isoxazoles from Nitroenamines and Aromatic Aldehydes

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Chinese Journal of Chemistry 2017年第10期35卷 1517-1521页

作者： Chao Lei Zhenhong Gao Xusheng Shao Xiaoyong Xu Zhong Li Shanghai Key Laboratory of Chemical Biology School of Pharmacy East China University of Science and Technology Shanghai 200237 China Shanghai Collaborative Innovation Center for Biomanufaeturing Technology Shanghai 200237 China

A novel approach for the synthesis of trisubstituted isoxazoles from nitroenamines and aromatic aldehydes is developed. L-Proline/potassium carbonate system was employed to promote this process. The reaction underwent nucleophilic attack of nitroenamines to aromatic aldehydes, intramolecular denitration, tautomerization and elimination of H2O to furnish the target compounds.

关键词： isoxazoles nitroenamines denitration heterocycles synthetic methods

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Copper Nitrate Mediated Cyclization of terminal Alkynes:Self-coupling reaction isoxazoles

Copper Nitrate Mediated Cyclization of terminal Alkynes:Self...

引用

河南省化学会2016年学术年会

作者： Lai Zhenzhen Xu Yuanqing Xu Hao Fang Xiaomin Ding Tao College of Chemistry and Chemical Engineering Henan University

isoxazoles have a wide variety of bioactivities, and widely applied in the field of medicines and pesticides. isoxazoles are an important class of N-heterocycles. isoxazoles are widely used in the synthesis of drug intermediates. In the pharmaceutical industry, isoxazoles as a variety of sterilization, disinfection of the main components of the drug. In agriculture, isoxazoles can inhibit the growth of weeds and soil bacteria, which also have a wide range of application value in the field of *** have been widely used in cross-coupling reactions, such as the Sonogashira reaction,and for the construction of various heterocycles, which have been reported to use the SO3/NO3-system in the reaction with alkynes for isoxazole syntheses starting from terminal alkynes. The method uses three sulfur dioxide, which has strong oxidation, strong corrosion resistance, and has certain harm to human body and environment. There was also reported terminal alkynes and nitric acid synthesis of isoxazoles. The using of strong acid, there may be the release of NO and NO2 in the reaction process, which caused pollution to the environment. Therefore, we are exploring copper nitrate mediated synthesis of isoxazoles(Figure 1). Copper nitrate are cheap,environmentally friendly, and safe to handle. Also the addition of additives has a good regional selectivity for the reaction. The significance of this transformation is threefold: The material is easy to obtain, the operation is simple, and the reaction condition is mild.

关键词： Copper Nitrate Self-coupling reaction isoxazoles

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