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A Case of Abnormal Bishler-Napieralski Cyclization Reaction,Leading to Form Benzyl oxazole Derivatives

Chinese Chemical Letters 2001年第3期12卷 195-196页

作者： Zhan Zhu LIU Shi Zhi CHEN Institute of Materia Medica Chinese Academy of Medical Sciences&Peking Union Medical CollegeBeijing 100050

A benzyl oxazole compound 3 was obtained with an excellent yield of 90% when N-acetyl-(2'-methoxy-4',5'-methylenedioxy)-phenylalanine methyl ester 1 was refluxed in POCl1/benzene. However, the anticipated product 3,4-dihydrosioquinoline-3-carboxylic acid methyl ester 2 could not be found. The mechanism was discussed in this article.

关键词： N-Acetyl amino acid oxazole Bishler-Napieralski reaction.

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Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp_(3))-H functionalization

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Chinese Chemical Letters 2024年第4期35卷 340-345页

作者： Tong Li Leping Pan Yan Zhang Jihu Su Kai Li Kuiliang Li Hu Chen Qi Sun Zhiyong Wang Hefei National Center for Physical Sciences at Microscale Key Laboratory of Precision and Intelligent ChemistrySchool of Chemistry and Materials ScienceUniversity of Science and Technology of ChinaHefei 230026China Anhui University of Science and Technology Huainan 232001China CAS Key Laboratory of Microscale Magnetic Resonance Department of Modern PhysicsUniversity of Science and Technology of ChinaHefei 230026China

An efficient N–H and C(sp~3)-H functionalization of aryl ketones with benzylamines/amino acids was developed under mild conditions by virtue of anodic oxidation. A variety of functionalized 2,5-diaryloxazoles were obtained with good to excellent yields. Moreover, some important natural products can be prepared by this method. The reaction features a broad substrate scope, scalability, metal-free and chemical oxidant-free.

关键词： Electrochemical Metal-free oxazole Oxidant-free

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Efficient synthesis and optical properties of coumarin derivatives containing oxazole ring moiety

Efficient synthesis and optical properties of coumarin deriv...

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中国化学会·第十六届全国有机合成化学学术研讨会

作者： Tianshuai Wang Junkai Ma Wei Xu Aihua Zheng 胡扬根 College of Pharmacy and Institute of Medicinal Chemistry Hubei University of Medicine Hubei Key Laboratory of Wudang Local Chinese Medicine Research 湖北医药学院

Coumarins represent a class of synthetically useful heterocyclic compounds that have been accredited with a broad range of biological/plarmacological action such as antimicrobial,antifungal,antiviral,anticoagulant,antitumor,and anti-inflammatory ***-crymarin derivatives have the superior thermal stability and outstanding optical properties,including extended spectral responses,high quantum yields,and superior photostability.[1] On the other hand,heterocycles containing the oxazole nucleus also exhibit various biological and optical activities.[2] The introduction of a oxazole ring to the coumarin system is expected to influence the biological/optical activities ***,we have been interested in the synthesis of fused pyrimidinones and imidazolones via aza-Wittig reaction,with the aim of evaluating their biological activities.[3,4]In our work,based on the structure of coumarin where there exists delocalization of π-electrons,a series of coumarin derivatives containing oxazole ring moiety were effectively synthesized by synthetic strategy of aza-Wittig reactions of functionalized iminophosphoranes（Fig.1）.Furthermore,their structures are confirmed by by NMR,EI-MS,IR and elementary *** addition,the optical properties including UV-vis/Fluorescence behavior performance are in progress.

关键词： Coumarins oxazole synthesis biological/optical activity

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Theoretical design of new bridge-ring insensitive high energy compounds by selected normal Diels-Alder reactions between NH_(2)-substituted oxazoles and NO_(2)/NF_(2)/NHNO_(2)-substituted ethylenes/acetylenes

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Defence Technology（防务技术） 2021年第5期17卷 1731-1739页

作者： Qiong Wu Qin-nan Hu Ming-quan Li Ze-wu Zhang Wei-hua Zhu Jiangsu Key Laboratory of Advanced Structural Materials and Application Technology School of Materials Science and EngineeringNanjing Institute of Technology1 Hongjing RoadNanjing211167China Institute for Computation in Molecular and Materials Science and Department of Chemistry Nanjing University of Science and TechnologyNanjing210094China

In this work,NH_(2)-substituted oxazoles and NO_(2)/NF_(2)/NHNO_(2)-substituted ethylenes/acetylenes were designed and used as dienes and dienophiles,respectively,in order to develop new bridge-ring insensitive high energy compounds through the Diels-Alder reaction between *** reaction type,reaction feasibility and performance of reaction products were investigated in detail *** results showed that dienes most possibly react with dienophiles through the HOMO-diene controlled normal Diels-Alder reaction at relatively low energy *** could react with the designed dienes much more easily than other dienophiles,and was employed to further design 29 new bridge-ring energetic *** to high heat of formation,density and oxygen balance,all designed bridge-ring energetic compounds have outstanding detonation performance,16 of them have higher energy than HMX(1,3,5,7-tetranitro-1,3,5,7-tetrazocine)and 2 others even possess comparative energy with the representative of high energy compounds CL-20(2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane).The predicted average h50 value of these bridge-ring energetic compounds is 83 cm,showing their low impact *** NH2 groups could obviously impel the proceeding of Diels-Alder reactions,but would slightly decrease the energy and sensitivity *** all,the new designed bridge-ring compounds have both high energy and low sensitivity,and may be produced through Diels-Alder reactions at relatively low energy *** paper may be helpful for the theoretical design and experiment synthesis of new advanced insensitive high energy compounds.

关键词： Diels-Alder Energetic compounds oxazole High energy Insensitive

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Design and Synthesis of Polyoxazole-based Macrocycles Tethered with a Phosphonate Group

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Chinese Journal of Chemistry 2014年第7期32卷 585-591页

作者： Fuling Qi Lianxun Gao Fushe Han Changchun Institute of Applied Chemistry Chinese Academy of SciencesChangchunJilin 130022China University of Chinese Academy of Sciences Beijing 100864China Key Lab of Synthetic Chemistry of Natural Substances Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

We present the design and synthesis of polyoxazole-based macrocycles containing a phosphonate group.A reliable route was established that allows for convenient and versatile incorporation of various phosphonate functionalities such as phosphonate ester,acid,and salt at the macrocyclic ring *** unprecedented macrocyclic compounds are anticipated to be appealing candidates as telomerase inhibitors.

关键词： telomerase Telomestatin oxazole phosphonate macrocyclic compound

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Iron-Promoted Practical One-Pot Synthesis of 2,5-Disubstituted oxazoles

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Chinese Journal of Chemistry 2012年第7期30卷 1464-1468页

作者：陈松辉白东虎时锋李健李春举贾学顺 Department of Chemistry Shanghai UniversityShanghai 200444China State Key Laboratory of Applied Organic Chemistry Lanzhou UniversityLanzhouGansu 730000China

A practical one-pot protocol for the synthesis of 2,5-disubstituted oxazoles from 1-aryl-2-nitroethanones was reported. In the presence of iron/AcOH in acetonitrile, the reaction of 1-aryl-2-nitroethanones with trimethyl orthoacetate or trimethyl orthobenzoate delivered the corresponding 2,5-disubstituted oxazoles in moderate to good yields.

关键词： oxazole iron one pot synthesis

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