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Synthesis of 3＇,4＇-Diaryl-4＇H-spiro[indoline-3,5＇-[1＇,2＇,4＇]- oxadiazol]-2-ones via DMAP-catalyzed domino reactions and Their Antibacterial Activity

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Chinese Journal of Chemistry 2016年第9期34卷 901-909页

作者： Guanghao Shi Xinwei He Yongjia Shang Liwei Xiang Cheng Yang Guang Han Bing Du Key Laboratory of Functional Molecular Solids Ministry of Education Anhui Key Laboratory of Molecule-Based Materials College of Chemistry and Materials Science Anhui Normal University Wuhu Anhui 241000 China Institute of Biomedical Sciences School of Life Sciences East China Normal University Shanghai 200241 China

A convenient and metal-flee DMAP-catalyzed domino reaction of isatins, arylamines and hydroximoyl chlorides has been developed to achieve 1,3-dipolar cycloaddition of imines into aryl nitrile oxides at ambient tempera- ture. In this one-pot transformation, a 1,2,4-oxadiazole skeleton was efficiently formed. This methodology needs no extra additives and features wide substrate scope, good functional group tolerance and mild reaction conditions. A plausible mechanism for this process was proposed. Moreover, the antibacterial activities of the products were evaluated towards Staphylococcus epidermidis, Staphylococcus aureus, Escherichia coli and Klebsiella pneumoniae using the Broth microdilution method.

关键词： 4-dimethylaminopyridine antimicrobial activity isatins domino reactions oxadiazoles

Gold Self-Relay Catalysis Enabling[3,3]-Sigmatropic Rearrange-ment/Nazarov Cyclization and Allylic Alkylation Cascade for Constructing All-Carbon Quaternary Stereocenters

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Chinese Journal of Chemistry 2022年第6期40卷 687-692页

作者： Fan-Tao Meng Xiao-Yan Qin Jing Li Tian-Shu Zhang Shu-Jiang Tu Bo Jiang Wen-Juan Hao School of Chemistry&Materials Science Jiangsu Normal UniversityXuzhouJiangsu 221116China School of Materials and Chemical Engineering Xuzhou University of TechnologyXuzhouJiangsu 221018China

Molecular scaffolds endowed with all-carbon quaternary stereocenter are ubiquitous in natural products and significant bioactive molecules.However,efficient construction of this type of structure units is full of challenge due to their congested chemical envi-ronment.Herein,we report a new gold(Ⅰ)self-relay catalysis merging[3,3]-sigmatropic rearrangement/Nazarov cyclization with al-lylic alkylation starting from 1,3-enyne acetates and allylic alcohols,producing a wide range of synthetically important allyl cyclo-pentenones with an all-carbon quaternary stereocenter in good yields under mild conditions.This protocol demonstrates the precise control of regioselectivity,high functional group tolerance of substrates and the low loading of gold catalyst without inert atmos-phere protection,providing a catalytic and efficient entry to all-carbon quaternary stereocenters.

关键词： Allylation domino reactions Carbocycles Gold self-relay catalysis 1,3-Enynes

Construction of Angularly Fused Tricyclic Compounds via Photo-induced Radical Cascade Cyclization

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Chinese Journal of Chemistry 2023年第19期41卷 2502-2506页

作者： Mengqin Hu Wei Cao Zhen Wang Yan Hao Ganxing Huang Yuqiao Zhou Song Qin Shaomin Fu Bo Liu Key Laboratory of Green Chemistry&Technology of Ministry of Education College of ChemistrySichuan UniversityChengduSichuan610064 China

Photo-induced electron transfer (PET) of silyl enol ethers has been employed to synthesize several fused ring systems. However, the method has limited applicability due to its narrow substrate scope, low product yields, unsatisfactory stereo- and regioselectivity. Herein, we report a PET-triggered cascade reaction of silyl enolates that leads to the formation of angularly fused tricyclic scaffolds. The reaction exhibits broad substrate scope and excellent stereoselectivity. The regio- and stereoselectivity of this cascade reaction is elucidated via DFT calculation and conformational analysis.

关键词： Cyclization Radical Tricyclic compounds Photocatalysis Enols Fused-ring systems domino reactions Regioselectivity

Palladium-Catalyzed Carbonylation of Multifunctionalized Substituted Alkynes to Quinolinone Derivatives under Mild Conditions

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Chinese Journal of Chemistry 2023年第23期41卷 3223-3228页

作者： Aleksandr Voronov Francesco Pancrazzi Ana Maria Constantin Raimondo Maggi Raffaella Mancuso Bartolo Gabriele Diego Olivieri Carla Carfagna Alessandro Casnati Francesco Rispoli Laura Baldini Nicola Della Ca Department of Chemistry Life Sciences and Environmental Sustainability (SCVSA)University of ParmaParco Area delle Scienze17/A43124 Parma (PR)Italy Center for Energy and Environment (CIDEA) University of ParmaParco Area delle Scienze 181/A43124 Parma (PR)Italy Laboratory of Industrial and Synthetic Organic Chemistry (LISOC) Department of Chemistry and Chemical TechnologiesUniversity of CalabriaVia P.Bucci 12/C87036 Arcavacata di RendeCosenza (CS)Italy Department of Biomolecular Sciences University of Urbino “Carlo Bo”Piazza Rinascimento 661029 Urbino (PU)Italy Department of Industrial Chemistry “T.Montanari” University of BolognaViale Risorgimento 440136 Bologna (BO)Italy

A highly selective palladium-catalyzed carbonylation of 2-alkynylanilines bearing an amide moiety to condensed six-membered heterocyclic structures has been developed under mild conditions(room temperature and atmospheric pressure of CO).The carbonylative protocol is also compatible with CO surrogates,such as benzene-1,3,5-triyl triformate(TFBen)or the newly developed calix[6]arenes functionalized with six formate groups(CLX[6]CO),which are both capable to release CO in situ.A series of tricyclic fused heterocycles containing the important oxazino-quinolinone scaffold have been selectively obtained(only the 6-endo-dig cyclization mode has been observed)in good to excellent yields(up to 99%).

关键词： Pd-catalysis Carbonylation Alkynes CO surrogates 6-endo-dig Calixarenes C1 building blocks domino reactions

One-pot synthesis of substituted 2-esteryl-3-acyl-1,5-benzodiazepines via three-component or domino reactions

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One-pot synthesis of substituted 2-esteryl-3-acyl-1,5-benzod...

Engaging Yne-Allenes in Cycloaddition reactions: Recent Developments

中国化学会·第十六届全国有机合成化学学术研讨会

作者： Laiyun Zhou Jingtian Chen 王兰芝 The College of Chemistry and Material Science Hebei Normal University 河北师范大学

1,5-Benzodiazepine is a kind of extremely significant compounds,which have high biologicaland pharmacological activity in the last decades. Previous studies on 1,5-benzodiazepines have indicated that free ester and acyl groups at different positions in the nuclei of the molecules can enhance the pharmacological properties of the compounds.2 Consequently,in view of our continuous interest in the synthesis of 1,5-benzodiazepine derivatives,we wished to synthesize 1,5-benzodiazepines with C2-position ester group and C3-position acyl group on the seven-membered ring structure.A multicomponent or domino reaction is one of the most desirable methods due to its efficient atom economy and green characteristics.3 Thus we have designed and one-pot synthesized a series of novel substituted 2-esteryi-3-acyl-1,5-benzodiazepines compounds via domino reactions(Scheme 1).The compound(1) was obtained by two nucleophilic substitution reactions of acetophenone and N.N-dimethylformamide dimethyl acetal with the removal of the methanol molecules.And then,the compounds(2) were synthesized via nucleophilic substitution reaction.Finally,the compounds(3) were obtained via nucleophilic addition,dehydration,cyclization and hydrogen transfer of compound(2) with ethyl pyruvate.Six target compounds(3) were finally obtained via above domino reactions with excellent yields(80%-92 %).These compounds are determined by H NMR,C NMR,MS,and IR.Simple operation,short reaction time,high yields are the advantages of this synthesis method.

关键词： 1,5-benzazepines one-pot synthesis domino reactions

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Chinese Journal of Chemistry 2022年第10期40卷 1224-1242页

作者： Jia-Yin Wang Wen-Juan Hao Shu-Jiang Tu Bo Jiang School of Chemistry&Materials Science Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional MaterialsJiangsu Normal UniversityXuzhouJiangsu 221116China

Yne-allenes bearing both a C-C triple bond and an allene unit are a class of focal substrates in organic synthesis,in view of their structure diversity,.high reactivity and intermediate variety in the past years.Engaging yne-allenes in numerous annulation cascades provides efficient and direct accesses to elaborate functionalized polycyclic molecular architectures in a convergent manner.There are lots of types of catalytic chemical reactions such as intramolecular cyclizations,cycloisomerizations,intermolecular annulations,and bicyclizations as well as tricyclizations with the assistance of Lewis acids,Bronsted acids,bases,transition metals,and otherr c atalysts.This review provides an overview of the chemistry developed with transformations of yne-allenes by discussing their general and specific reactivities,presenting and commenting on their mechanisms as well as their applications.

关键词： Yne-alenes Cycloaddition domino reactions Carbocycles Heterocycles

[4+3]Cycloaddition of ketenimines with furocarbenoids:Divergent and efficient synthesis of fused cycloheptatriene and tropone scaffolds

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Chinese Chemical Letters 2023年第5期34卷 227-231页

作者： Jin Wang Zhaoyang Li Shengxin Bai Qinghua Zhou Tengteng Wu Zhongyan Hu Xianxiu Xu Chemical Engineering and Materials Science Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of ShandongKey Laboratory of Molecular and Nano ProbesCollege of ChemistryMinistry of EducationInstitute of Molecular and Nano ScienceShandong Normal UniversityJi’nan 250014China

An unprecedent[4+3]cycloaddition of furoketenimines with furocarbenoids has been disclosed for the divergent and efficient synthesis of cycloheptafuran and cycloheptapyrrole scaffolds.Zinc chloride acted as promoters for both the formation of these two transient intermediates from isocyanides and ene-yne-ketones,and the subsequent construction of seven-membered ring.Three rings and five bonds were constructed successively in this three-component one-pot domino reaction.

关键词： domino reactions Isocyanides Ene-yne-ketones Cycloheptafuran scaffolds [4+3]cycloaddition

Copper-catalyzed chemoselective heterocyclization of two isocyanides:Facile access to pyrroloazepinone derivatives

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Chinese Chemical Letters 2023年第2期34卷 202-205页

作者： Xiaoyu Guo Jinhuan Dong Yunjie Zhu Lan Bao Zhongyan Hu Xianxiu Xu College of Chemistry Chemical Engineering and Materials ScienceCollaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of ShandongKey Laboratory of Molecular and Nano ProbesMinistry of EducationInstitute of Molecular and Nano ScienceShandong Normal UniversityJi'nan 250014China

A Cu-catalyzed chemoselective heterocyclization of o-cinnamoyl arylisocyanides with α-substituted tosylmethyl isocyanides is developed for the efficient synthesis benzopyrroloazepinones. An isocyanide insertion into ... 详细信息

关键词： Isocyanides domino reactions Pyrroloazepinones

Recent Advances in domino Synthesis of Fused Polycyclic N-Heterocycles Based on Intramolecular Alkyne Hydroamination under Copper Catalysis

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Chinese Journal of Chemistry 2023年第24期41卷 3751-3771页

作者： Zefeng Jin Guodong Shen Xin Lv Key Laboratory of the Ministry of Education for Advanced Catalysis Materials College of Chemistry and Materials ScienceZhejiang Normal UniversityJinhuaZhejiang321004 China School of Chemistry and Chemical Engineering Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell TechnologyLiaocheng UniversityLiaochengShandong252059 China

Fused polycyclic N-heterocycles are very important scaffolds in biomedicinal chemistry and materials science.Intramolecular alkyne hydroamination is a powerful method for the construction of N-heterocycles.In the last two decades,copper-catalyzed domino reactions based on intramolecular alkyne hydroamination has emerged as a robust strategy for assembling various fused polycyclic N-heterocycles.Great progress has been achieved in this area.This short review covers the advances made in copper-catalyzed domino synthesis of fused polycyclic N-heterocycles based on the strategy from 2008 to 2023,and will hopefully serve as an inspiration towards the exploration of new copper-catalyzed versions of the transformation.The domino transformations are introduced and discussed from five aspects according to the different key processes involved in these reactions.

关键词： domino reactions Polycyclic N-heterocycles Fused-ring systems Intramolecular hydroamination Alkynes Copper Cyclization Synthetic methods