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Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles

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Chinese Chemical Letters 2024年第4期35卷 330-335页

作者： Yaping Zhang Wei Zhou Mingchun Gao Tianqi Liu Bingxin Liu Chang-Hua Ding 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 UniversityShanghai 200444China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

A facile Tf OH-catalyzed oxidative cyclization of allyl compounds and isocyanide has been developed with the assistance of DDQ, where isocyanide is used as the crucial "N" and "CN" sources. Highly functionalized 2-cyanopyrroles are constructed efficiently through a new formal [3 + 2] mode, demonstrating diverse reactivity and synthetic utility in organic chemistry. 2-Cyanopyrrole is converted into a nucleobase analogue of Remdesivir and 5H-pyrrolo[2,1-a]isoindole through a three-step or a two-step sequence, respectively. This protocol features broad substrate scope, operational simplicity and good functional group tolerance.

关键词： isocyanide Cyanopyrrole Insertion Allyl compound Bronsted acid catalysis

Facile Mechanochemical Preparation of Polyamide-derivatives via Solid-state Benzoxazine-isocyanide Chemistry

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Chinese Journal of Polymer Science 2021年第5期39卷 573-584,I0006页

作者： Xu Sun Wei Shi Xin-Yu Zhou Sheng Ding Oil&Gas Field Applied Chemistry Key Laboratory of Sichuan Province College of Chemistry and Chemical EngineeringSouthwest Petroleum UniversityChengdu 610500China

With the exploration of novel sustainable protocol for functional polyamides'(PAs)construction as the starting point,herein,the small molecular model compound(M 1-ssBIC)was prepared firstly by manual grinding of monofunctional benzoxazine(1a)and isocyanide(1 b)via solid-state benzoxazine-isocyanide chemistry(ssBIC)to evaluate the feasibility of *** PAs(P1-series polymers)were subsequently synthesized from biunctional benzoxazine(2a)and isocyanide(2b),and the influence of the loading of catalyst(octylphosphonic acid)(OPA)on the polymerization was ***,two kinds of cross-linked PAs were successfully constructed via ssBIC by using trifunctional benzoxazine(3a)and cross-linked polybenzoxazine(4a)as reaction substrates,respectively,thus verifying the adaptability of *** characterization indicates that amide,phenolic hydroxyl and tertiary amine substructures,with metal-complexing capability,have been successfully integrated into the obtained PAs.A type of representative PA/silver composite(P3-AgNPs)was prepared subsequently via in situ reduction treatment,and its application as recyclable reduction catalyst for organic pollutant p-nitrophenol(4-NP)was preliminarily investigated here to provide the example for possible downstream application of *** think that this current work could provide a new pathway for the construction of functional PAs through facile and sustainable ssBIC protocol.

关键词： Mechanochemistry Solid-state synthesis Benzoxazine isocyanide Polyamide

Investigation of the Adsorption and Self Assembly of isocyanide Derivatives on Au（111） Surface

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Chinese Journal of Chemistry 2007年第9期25卷 1223-1228页

作者：周俊红史良伟张涛陈敏伯 School of Chemistry and Molecular Engineering East China University of Science and Technology Shanghai 200237 China Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China

The adsorption and self-assembly of isocyanide derivatives on Au（111） surface were investigated by density functional theory （DFF） and molecular dynamics simulation. The calculation for phenyl isocyanide by DFT was based on cluster and slab models. The self-assembled monolayers of 2-isocyanoazulene and 1,3-diethoxycarbony 1- 2-isocyanoazulene on Au（111） were simulated using Au-C force field parameters developed by us. It was found that the top site was the most preferred position, and the isocyanoazulene and its derivatives could form the ordered face to edge self-assembled monolayer on gold surface indeed, and the molecules stood on the gold surface vertically.

关键词： isocyanide Au(111) density functional theory molecular dynamics simulation

Luminescent Tetranuclear Copper(I) Phenylacetylide Complex with Cyclohexyl isocyanide

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Chinese Journal of Structural Chemistry 2005年第1期24卷 13-16页

作者：施林熙张礼仪陈忠宁 State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of Matter The Chinese Academy of Sciences Fuzhou Fujian 350002 China

Depolymerizing copper(I) phenylacetylide [Cu(C≡CPh)]n with cyclohexyl isocy- anide (CNCy) gave a tetranuclear copper(I) complex Cu4(CNCy)4(μ-η1-C≡CPh)2(μ3-η1,η1, η2-C≡ CPh)2. Crystal data: C30H32Cu2N2, Mr = 547.66, space group P1, a = 8.6448(1), b = 11.5772(2), c = 14.6666(4) ?, α = 88.387(2), β = 86.826(2), γ = 68.222(1)°, V = 1360.97(5) ?3, Z = 2, F(000) = 568, Dc = 1.336 g/cm3, μ = 1.582 mm-1, the final R = 0.0629 and wR = 0.1282 for 3257 observed reflections with I > 2σ(I). The phenylacetylide adopts μ-η1 and μ3-η1,η1,η2 bonding modes. The compound shows intense luminescence in the solid state.

关键词： acetylide copper isocyanide luminescence

isocyanide-Based Multicomponent Reactions and Some Related Cycloaddition Reactions

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Isocyanide-Based Multicomponent Reactions and Some Related C...

isocyanide-Based Domino Reactions to Synthesize Polycyclic Skeletons

中国化学会全国第十一届有机合成化学学术研讨会

作者：李健上海大学理学院化学系

isocyanide-based multicomponent reactions(IMCRs)have been widely investigated in organic synthesis owing to their inherent features such as atom-and step economy,convergence and diversity. In particular,IMCRs enjoy unique superiority over traditional methods for the rapid and efBcient generation of structurally complex molecules. Recently,we have focused our attention on multicomponent reactions involving isocyanide and allenoate,thus providing a quick access to synthesize five-membered carbocycles and heterocycles. In this process,some interesting cycloaddtion reactions are also observed.

关键词： isocyanide Multicomponent reaction Allenoate Cycloaddition

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Isocyanide-Based Domino Reactions to Synthesize Polycyclic S...

Exploring New Reactions involving isocyanide

中国化学会第十三届全国有机合成化学学术研讨会

作者：李健上海大学化学系

Ever since the Passerini and Ugi reactions were reported,isocyanides have found wide application in a variety of carbon-carbon and carbon-heteroatom bond-forming reactions.1 In particular,they are found to be particularly compatible for the rapid and efficient construction of heterocycles with increased complexity and diversity.2 In the past years,we have been particularly interested in isocyanide chemistry and have focused our attention on the development of isocyanide-based novel transformations.3 Thus,a series of novel strategies have been developed toward the construction of a series of drug-like heterocycles using isocyanide as versatile building *** a continuation,4 herein we wish to report that isocyanides can serve as versatile building blocks to synthesize many structurally unusual polycyclic skeletons including spioxindole and 1,9-dihydropyrano[3,4-b]indole in an efficient manner.

关键词： isocyanide polycyclic skeleton domino reaction spirooxindole

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Exploring New Reactions involving Isocyanide

Mn(Ⅲ)-mediated radical cascade reaction of boronic acids with isocyanides:Synthesis of diimide derivatives

中国化学会全国第十一届有机合成化学学术研讨会

作者： Yong Wang Jiangling Peng Ziwei Hu Jian Lei Zhonghua Xia Jian Wang Jing Li Qiang Zhu State Key Laboratory of Respiratory Disease Guangzhou Institutes of Biomedicine and HealthChinese Academy of Sciences

isocyanides have been recognized as versatile building blocks in Lewis or Bronsted acid-promoted reactions,including Passerini and Ugi mutlicomponent reactions,complex amide synthesis and ***,their application in transition-metal-catalyzed imination,carboxyamidation,amidination reactions,and cyanation,acting as isoelectronic equivalents of CO,is relatively *** this conference,we will report our recent research on some new reactions involving imidoyl palladium and imidoyl radical intermediates for the synthesis of N-heterocycles.

关键词： isocyanide Palladium Imidoyl radical Heterocycle

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Chinese Chemical Letters 2019年第2期30卷 379-382页

作者： Fei Wang Tian-Qi Wei Pei Xu Shun-Yi Wang Shun-Jun Ji Key Laboratory of Organic Synthesis of Jiangsu Province College of ChemistryChemical Engineering and Materials Science ξ Collaborative Innovation Center of Suzhou Nano Science and Technology Soochow University

A manganese (Ⅲ)-promoted oxidative radical cascade reaction of easily accessible arylboronic acids with isocyanides to construct diimide derivatives was studied. This protocol provides a new way to synthesis of acety... 详细信息

关键词： Mn(OAc)3 isocyanide Arylboronic acid Diimide derivatives Radical cascade

Cobalt（Ⅱ）-Catalyzed Bis-isocyanides Insertion Reactions with Boric Acidsand Sulfonyl Azides via Nitrene Radical Coupling

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Chinese Journal of Chemistry 2018年第11期36卷 1011-1016页

作者： Zheng-Yang Gu Rong Zhang Shun-Yi Wang Shun-Jun Ji Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology Soochow University Suzhou Jiangsu 215123 China

A Co(II)‐catalyzed effective synthesis of amidinium imine derivatives from the reaction of isocyanides and boric acids using organic azides as nitrene source has been developed. This protocol provides a new, environment‐friendly and simple strategy to construct amidinium imine derivatives with a range of substrates without any oxidants and additives.

关键词： Co(II)‐catalysis isocyanide boric acids azides nitrene radical C1 building blocks