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Chinese Journal of Chemistry 2024年第3期42卷 271-275页

作者： Yannan Zhu Haoran Jiang Yi-Ning Wang Faculty of Chemistry and Chemical Engineering Yancheng Institute of TechnologyYanchengJiangsu224051 China

A phosphine-catalyzed [4+3] annulation between dinucleophilic indole derivatives and Morita−Baylis−Hillman (MBH) carbonates was discovered by using the N1 and N4′/C4′ nucleophilicities of the indole precursors,in which indoles act as four atom synthons. This protocol provides an efficient and facile access to indole-1,2-fused 1,4-diazepinones and azepines in good to high yields in one step,which illustrates potential synthetic utilities in drug discovery.

关键词： Phosphine catalysis [4+3]Annulation Indole derivatives nitrogen heterocycles Organocatalysis

Asymmetric Hydrogenation of Phenanthridines with Chiral Boranes

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Chinese Journal of Chemistry 2024年第6期42卷 631-635页

作者： Guangyu Cui Xiangqing Feng Haifeng Du Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and FunctionInstitute of ChemistryChinese Academy of SciencesBeijing100190 China University of Chinese Academy of Sciences Beijing100049 China

The asymmetric hydrogenation of N-heteroarenes provides an efficient method for the synthesis of optically active cyclic secondary *** this paper,we described an asymmetric hydrogenation of phenanthridines using a chiral mono-alkene-derived borane.A variety of dihydrophenanthridines were furnished in high yields with up to 93%*** current catalytic system was very sensitive for the steric hindrance of *** substituents at one phenyl group of phenanthridines were required to obtain the high *** large substituents on the carbon of the C=N bonds would diminish the reactivity sharply.

关键词： Asymmetric catalysis Hydrogenation nitrogen heterocycles Phenanthridines Frustrated Lewis pairs Chiral boranes

1,3-Dipolar Cycloaddition of Polycyclic Aromatic Azomethine Ylides and Alkynylbenziodoxoles for Synthesis of Functional Dibenzoullazines

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Chinese Journal of Chemistry 2024年第10期42卷 1079-1083页

作者： Hui Han Glen Wee Zhuan Goh Yongxin Li Naohiko Yoshikai Shingo Ito Schoolof Chemistry ChemicalEngineering and BiotechnologyNanyang Technoogical University21 Nanyang LinkSingapore 637371Singapore Graduate School of Pharmaceutical Sciences Tohoku UniversitySendai 980-8578Japan

A new family of dibenzoullazine derivatives was synthesized through 1,3-dipolar cycloaddition of polycyclic aromatic azomethine ylides with alkynylbenziodoxoles followed by *** benziodoxole moiety in the resulting products was used as a versatile linchpin for the synthesis of structurally diverse functional dibenzoullazines that are difficult to access by other synthetic methods.

关键词： Cycloaddition nitrogen heterocycles Azomethine ylides Hypervalent compounds Dibenzoullazine

Recent advances in visible-light photoredox-catalyzed nitrogen radical cyclization

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Green Synthesis and Catalysis 2020年第1期1卷 42-51页

作者： Pengzi Wang Quanqing Zhao Wenjing Xiao Jiarong Chen CCNU-uOttawa Joint Research Centre Key Laboratory of Pesticides&Chemical Biology Ministry of EducationCollege of ChemistryCentral China Normal UniversityWuhan 430079China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryShanghai 200032China

Visible-light photoredox catalysis is a powerful and attractive strategy for organic molecule activation and new reaction design owing to its environmental-friendly characteristics and unique catalytic mechanisms,and has found wide applications in organic *** catalytic strategy enables controllable generation of diverse nitrogen-centered radicals(NCRs)under mild conditions,providing access to construction of diverse nitrogencontaining *** this review,we critically illustrate the recent advances in the field of visible-light photoredox-catalyzed cyclization of nitrogen-centered radicals,based on the different radical precursors and activation *** possible,particular emphasis is also put on working models and synthetic applications.

关键词： Photoredox catalysis nitrogen radicals Radical cyclization reactions nitrogen-containing compounds nitrogen heterocycles

Metal-Free Synthesis of Benzo[a]phenanthridines from Aromatic Aldehydes,Cyclohexanones,and Aromatic Amines

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Chinese Journal of Chemistry 2022年第3期40卷 365-370页

作者： Pingyu Jiang Zhifei Shan Shanping Chen Quanyuan Wang Shuxin Jiang Haolin Zheng Guo-Jun Deng Key Laboratory for Green Organic Synthesis and Application of Hunan Province Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of EducationCollege of ChemistryXiongtan UniversityXiangtanHunon 411105China Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates(South China University of Technology) GuangzhouGuangdong 510640China

A three-component synthesis of benzo[a]phenanthridines from aromatic aldehydes,cyclohexanones,and aromatic amines has been developed,which is mediated by KI/DMSO/camphorsulfonic acid to afford a variety of functionalized benzo[a]phenanthridines in satisfactory *** present strategy provides a biaryl motif ortho to the nitrogen atom which has the potential to be used as ligand by further *** the advantages of readily available starting materials,transition-metal-free conditions,gram-scale synthesis,and broad substrate scope,this three-component protocol provides an efficient approach for the preparation of diverse benzo[a]phenanthridines.

关键词： nitrogen heterocycles Multicomponent reactions Dehydroaromatization Cyclization Metal-free

A New Polynitrogen-Heterocyclic Scaffold 2,4,6,8-Tetraazanoradamantane Skeleton:Synthesis and Conversion of Its Functionalities

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Chinese Journal of Chemistry 2023年第7期41卷 783-789页

作者： ongbin Cai Bing Li Tianjiao Hou Qi Zhou Yunzhi Liu Huan Li Yuan Gao Longyi Zhu Jun Luo School of Chemistry and Chemical Engineering Nanjing University of Science and TechnologyNanjingJiangsu210094 China College of Chemical Engineering Nanjing Tech UniversityNanjingJiangsu211816 China

Comprehensive Summary 2,4,6,8-Tetraazanoradamantane skeleton is a unique rigid cage-like organic structure that has not been *** this article,a facile protocol to build all-bridge-position-functionalized 2,4,6,8-tetraazanoradamantane skeleton by condensation of glyoxal,primary amines and disubstituted malondialdehydes,which were in situ generated from 2,2-dipropenyl-1,3-dioxolane or 4,4-dimethoxyhepta-2,5-diene via ozonation,is reported for the first time.A variety of primary amines are compatible with this process,and the corresponding 2,4,6,8-tetraalkyl-2,4,6,8-tetraazanoradamantane-9-one ethylene or methyl ketals were achieved in 16%—58%yields.N-Benzyl group could be converted to other functionalities such as acetyl and nitro,which indicates the structural diversity of this scaffold.

关键词： Cage compounds Tetraazanoradamantane Multicomponent reactions nitrogen heterocycles Condensation

3,6-bis(2,2,2-trinitroethylnitramino)-1,2,4,*** and energy abilities as a component of solid composite propellants

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Defence Technology（防务技术） 2022年第7期18卷 1148-1155页

作者： Anatoly G.Korepin Natalia M.Glushakova David B.Lempert Anatoly I.Kazakov Gennady V.Shilov Denis V.Korchagin Vadim M.Volokhov Elena S.Amosova Sergey M.Aldoshin Institute of Problems of Chemical Physics Ac.Semenov Avenue 1Chernogolovka142432Russian Federation

The work addresses to the study of the molecular and crystal structure and properties of a new energyintensive compound 3,6-bis(2,2,2-trinitroethylnitramino)-1,2,4,5-tetrazine(NBTAT),first obtained by the authors in *** compound crystallizes in the monoclinic system,space group P2(1)/n,density at room temperature 1.939 g/cm^(3).The energies of crystal packing and pairwise intermolecular interactions in NBTAT and its unnitrated analogue BTAT were calculated,and their comparative analysis was carried *** enthalpy of formation of NBTAT molecules was calculated by quantum-chemical methods using Gaussian 09,and the enthalpy of formation of NBTAT in the solid phase(618 kJ/mol)was *** energy capabilities of NBTAT as an oxidizer of solid composite propellants are *** is shown that in metal-free compositions NBTAT is significantly superior to ammonium perchlorate(AP),dinitramide ammonium salt(ADN),HMX,BTAT at all stages of rocket systems,and is comparable to the superdense CL-20 yielding to the latter at the lower stages and slightly winning at the upper stages.

关键词： nitrogen heterocycles Quantum chemistry Enthalpy of formation 3,6-bis(2,2,2-trinitroethylnitramino)-1,2,4,5-tetrazine Crystal structure Energetic ability

Bischler-Napieralski Cyclization:A Versatile Reaction towards Functional Aza-PAHs and Their Conjugated Polymers

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Chinese Journal of Chemistry 2021年第11期39卷 3101-3112,3113-3114,3115页

作者： Mengwei Li Yuan Yuan Yulan Chen Institute of Molecular Plus Department of ChemistryTianjin UniversityTianjin300354 China

nitrogen atom doped polycyclic aromatic hydrocarbons,the so-called aza-PAHs,and their conjugated polymers are applicable as functional chromophores and organic *** developments of PAHs and heterocyclic chemistry have been made possible by considerable improvements in synthetic methodologies,among which one-step reactions leading directly to an aza-conjugated ring are highly ***-Napieralski cyclization,an old yet efficient reaction,can accomplish this *** the last ten years,this reaction has been successfully used to synthesize a great variety of aza-PAHs *** combination with polymer chemistry is able to provide the corresponding *** feature article summarizes the up-to-data advances,mainly achieved by our groups,on the design and synthesis of new and well-tailored aza-PAHs and macromolecular architectures using Bischler-Napieralski cyclization as the key ***,the versatile applications of these functional materials in the fields of chemosensors,optoelectronic devices,and biomolecular probes are also covered in detail.

关键词： Bischler-Napieralski cyclization Aza-PAHs Conjugated polymers Fluorescence nitrogen heterocycles Synthetic methods

Transition-Metal-Free Catalyzed Dehydrative Coupling of Quinoline and Isoquinoline N-Oxides with Propargylic Alcohols

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Chinese Journal of Chemistry 2022年第1期40卷 71-78页

作者： Zhao-Nan Cai Xiang-Xuan Feng Yuecheng Zhang Cong-Cong Lu Ya-Ping Han Jiquan Zhao School of Chemical Engineering and Technology Hebei University of TechnologyTianjin 300130China

A novel,green,and transition-metal-free protocol for the facile modification of quinoline and isoquinoline derivatives is introduced,starting from readily available and environmentally benign quinoline and isoquinoline N-oxides with propargylic alcohols in the presence of Na_(2)S_(2)O_(8) or K_(2)S_(2)O_(8) at 100℃.The one-pot transformation features the advantages of good functional group compatibility,short reaction time,operational simplicity,and highly efficient reaction *** protocol,which produces water as the only byproduct,provides efficient and atom-economical access to a class of fascinating quinoline and isoquinoline products in satisfactory *** method is effective on the gram scale,thus highlighting the inherent practicality of this methodology.

关键词： Synthetic methods Alcohols nitrogen heterocycles Transition-metal-free Solvent-free

Rhodium-Catalyzed Direct C-H Alkenylation of Indoles with Alkenyl Borates

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Chinese Journal of Chemistry 2021年第10期39卷 2823-2828页

作者： Ze-Tian Wang Zi-Ang Zheng Peng-Jie Li Chun-Ni Zhou Shao-Jun Cai Biao Xiao Liang Wang Key Laboratory of Optoelectronic Chemical Materials and Devices Ministry of EducationSchool of Chemical and Environmental EngineeringJianghan University8 Sanjiaohu RoadWuhanHubei430056 China

Main observation and conclusion A new Rh(Ⅲ)-catalyzed direct C—H alkenylation of 2,3-unsubstitued indoles with alkenyl borates through C—H activation followed by transmetallation was *** protocol provides an efficient method for the synthesis of terminal C2-alkenylindoles under mild conditions,and also shows broad substrate scope and high functional group tolerance with respect to both ***,the C2-alkenylated indole can be easily transformed into carboline derivative,which is an important polycyclic indole moiety in natural products and drug molecules.

关键词： Rhodium C-H activation Terminal alkenylindoles Alkenyl borates nitrogen heterocycles