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Metallaphotoredox-Catalyzed Three-Component Couplings for Practical Synthesis of ureas and Carbamates

Chinese Journal of Chemistry 2024年第3期42卷 264-270页

作者： Ernest Koranteng Zhen-Cao Shu Yi-Yin Liu Qian Yang Bin Shi Qiang-Xian Wu Fen Tan Liang-Qiu Lu Wen-Jing Xiao Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction Ministry of EducationCollege of ChemistryCentral China Normal University152 Luoyu RoadWuhanHubei430079 China Wuhan Youji Industries Co. LtdNo.1 2nd Chemical Rd.WuhanHubei430082 China Hubei Key Laboratory of Purification and Application of Plant Anti-cancer Active Ingredients School of Chemistry and Life SciencesHubei University of EducationWuhanHubei430205 China State Key Laboratory for Oxo Synthesis and Selective Oxidation Lanzhou Institute of Chemical PhysicsChinese Academy of SciencesLanzhouGansu730000 China School of Chemistry and Chemical Engineering Henan Normal UniversityXinxiangHenan453007 China Wuhan Institute of Photochemistry and Technology WuhanHubei430082 China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai200032 China

ureas are widely used in drugs,materials and catalysts because of their diamide structure,which can form strong hydrogen ***,it is of great scientific significance to develop efficient and green methods for the synthesis of urea compounds,especially unsymmetrical ***,we have disclosed novel and highly efficient three-component coupling reactions of organic halides,sodium cyanate and amines enabled by nickel/photoredox dual catalysis for the preparation of unsymmetrical *** reaction features simple and safe operations,broad substrate scopes,and product *** allows the facile synthesis of N-aryl/vinyl ureas from readily available,user-friendly feedstocks under mild conditions(27 examples,36%—98%yields).In addition,this method is further derived to alcohols as nucleophiles to synthesize a series of carbamates(15 examples,40%—95%yields).The mechanism experiment shows that the isocyanate produced by the coupling of halide and sodium cyanate may be the key intermediate in this reaction.

关键词： Cross-coupling Nickel Photoredox catalysis Three-component reaction ureas Carbamates

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KI Catalyzed Nitrogenation of Aldehydes and Alcohols： Direct Synthesis of Carbamoyl Azides and ureas

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Chinese Journal of Chemistry 2017年第6期35卷 845-848页

作者： Song Song Peng Feng Miancheng Zou Ning Jiao State Key Laboratory of Natural and Biomimetic Drugs School of Pharmaceutical Sciences Peking University Beijing 100191 China Shanghai Key Laboratory of Green Chemistry and Chemical Processes East China Normal University Shanghai 200062 China

An efficient KI catalyzed nitrogenation of aldehydes and alcohols for the direct synthesis of carbamoyl azides and ureas via a radical process has been developed. The simple operating procedures, the readily available starting materials including aldehydes, alcohols and amines, as well as the utility of the products all make this strategy very attractive.

关键词： nitrogenation aldehydes carbamoyl azides ureas KI TBHP

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A　NEW　SYNTHESIS　OF　1,4-DISUBSTITUTED　AZO　ureas

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Chinese Chemical Letters 1996年第5期7卷 393-394页

作者： Jian Ping LI Jin Ye WANG Dong Lan MA Yu Lu WANG (Department of Chemistry, Henan Normal University, Xinxiang, 453002)(photobiology Group, photodynamics Research Center, The Institute of Physical and Chemical Research, 19-1399 Koeji, Nagamachi, Aoba-ku, Department of Chemistry Henan Normal University Xinxiang 453002 Photobiology Group Photodynamics Research Center Inst. of Phys. and Chemical Research 19-1399 Koeji Nagamachi Aoba-ku Sendai 980 Japan

Abstract: Ten new 1, 4-disubstituted azo ureas were synthesized by the reaction of substituted semicarbazide compounds with a phenoxyl radical between two phases in good yield.

关键词： AZO ureas SYNTHESIS OF DISUBSTITUTED NEW

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Studies on the Solvent Effect of N-Carbamoyl-N-(1-Oxyl 2,2,5,5-Tetramethyl-Pyrrolin-3-yl) ureas

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Chemical Research in Chinese Universities 1990年第1期6卷 20-27页

作者： Zhang Ziyi and Wei Lulin (Department of Chemistry, University of Lanzhou, Lanzhou)Wang Hanqing (Lanzhou Institute of Chemical Physics, Acoiemia Sinica, Lanzhou)

The electron spin resonance spectra of N-carbamoyl-N-(l-oxyl-2,2,5,5-tetramethyl-pyrrolin-3-yl) urea compounds in ten solvents with different polarities were determined. It was found that the hyperfine splitting constant AN and spin density pN. as well as the energy difference between two adjacent energy levels E of different pyrroline nitroxides in the same solvent increase with the increase of electron-withdrawing α-bility of the substituted groups on the aromatic ring. There was a linear correlation between AN and Reichardt ET value, and between AN and Z value as well. Such a linear correlation was also found between solvent viscosity n and ESR rotational correlation time r. On the other hand, the correlation between T and the relative height hr of peak on high field was reverse. The results are discussed in the paper.

关键词： Solvent effect ureas Pyrroline nitroxides

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Anion recognition with porphyrin-bottomed tetraurea receptors

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Chinese Chemical Letters 2018年第9期29卷 1372-1374页

作者： Wei Lin Tian-Yong Cen Shu-Ping Wang Zibin Zhang Jing Wu Jianying Huang Shijun Li College of Material Chemistry and Chemical Engineering Hangzhou Normal University Hangzhou 310036 China College of Food Science and Biotechnology Zhejiang Gongshang University Hangzhou 310035 China

Three tetraurea-appended porphyrin derivatives were synthesized and applied as anion receptors to complex with various anions, including F^-, Cl^-, Br^-, I^-, NO3^-, HSO4^-, and AcO^-. The binding stoichiometries were all measured to be 1：1 and high binding abilities of these receptors toward the anions were demonstrated with the association constants of up to 1.1 × 10^8 L/mol. The complexation of the receptors with anions was further unambiguously confirmed by single-crystal X-ray analysis

关键词： Host-guest chemistry Anion receptors Porphyrins Molecular recognition ureas Supramolecular chemistry

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Efficient Synthesis of 2-Arylamino-2-imidazolines and 2-Aminobenzimidazoles with Aminoiminomethanesulfonic Acid Derivatives

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Chinese Journal of Chemistry 2011年第5期29卷 1055-1058页

作者： Mohanazadeh Farajollah Nami Navabe Hosseini Samine Sadat Institute of Industrial Chemistry Iranian Research Organization for Science and Technology Tehran Iran Department of Chemistry Azad Islamic University Babol lran

A highly efficient synthesis of 2-arylamino-2-irnidazolines and 2-aminobenzimidazoles from aminoiminomethanesulfonic acid derivatives is described. The method is simple and practical, generating imidazoline and benzim... 详细信息

关键词： 2-arylamino-2-imidazoline 2-aminobenzimidazole synthesis cyclization heterocycle aminoimi nomethanesulfonic acid ureas

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