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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

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...

Total Synthesis and Stereochemical Assignment of Talaroconvolutin A and Talarofuranone: Gram-scale Synthesis of Ferroptosis Inducer Talaroconvolutin A

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 *** then,the compounds(2) were synthesized via nucleophilic substitution ***,the compounds(3) were obtained via nucleophilic addition,dehydration,cyclization and hydrogen transfer of compound(2) with ethyl *** 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 *** 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 2024年第13期42卷 1509-1514页

作者： Ming Yao Wei Yang Jing Li Chengyun Huang Jin Fang Sulu Qin Shuzhi Liu Xiaolong Yang School of Pharmaceutical Sciences South-Central Minzu UniversityWuhanHubei 430074China

The first total synthesis of talaroconvolutin A(1.1 g obtained)and talarofuranone has been achieved using accessible materials(12 steps,7.5%and 8.2%yields,respectively).Convergent routes involved intramolecular Diels-Alder reactions in two approaches for creating the decalin ***,an unprecedented DMP-mediated domino reaction resulted in the deoxy-tetramic acid *** syntheses not only establish the absolute configuration of talaroconvolutin A but also enable further collaborative studies of this typeofferroptosisinducers.

关键词： Natural products Aldehydes Total synthesis domino reactions Biological activity Antitumor agents Ferroptosis Diels-Alder reaction Talaroconvolutin A

Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides:Access toα-ketoamide peptidomimetics

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Chinese Chemical Letters 2024年第6期35卷 320-326页

作者： Yue Sun Liming Yang Yaohang Cheng Guanghui An Guangming Li School of Chemistry and Materials Science Heilongjiang UniversityHarbin 150080China

We report the unprecedent Pd(I)catalyzed ring-opening arylation of cyclopropyl-α-*** protocol allows facile access to biologically important α-ketoamide-containing oligopeptides and even more challenging peptide-natural product *** selectivity was achieved by introduction of special unnatural amino acids,which also meets the requisite of bioorthogonal *** investigations reveals a distinct domino radical ring-opening process through Pd(I)catalysis.

关键词： Pd(I)catalysis Ring-opening arylation domino reactions Oligopeptides Late-stage functionalization

Chemodivergent Synthesis of Benzofurans and 2,3-Dihydrobenzofurans via Tandem Oxidative Annulation of Enaminones and Salicylaldehydes

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Chinese Journal of Chemistry 2024年第15期42卷 1727-1733页

作者： Xiyan Duan Hui Li Junqi Wang Kun Liu Meixin Shi Weidong Lian Ran Chen Pu Liu School of Chemistry&Chemical Engineering Henan University of Science and TechnologyLuoyangHenan 471003China

Chemodivergent synthesis of benzofurans and 2,3-dihydrobenzofurans has been *** a reaction system consisting of DBDMH and K_(2)CO_(3) as promotors,controlled conditions enabled the formation of two sets of valuable heterocycles from the tandem transformation of enaminones and *** key to success was the identification of the reaction parameters,in which the imine intermediate which was formed by transient halogenation coupling and substitution processes underwent either aldol condensation/annulation or imine hydrolysis/aldol *** additives NH_(4)Cl or Fe_(2)(SO_(4))_(3) controlled the unique selectivity of this reaction.A broad substrate scope of enaminones and salicylaldehydes has been employed in this reaction,demonstrating excellent functional group tolerance and versatility.

关键词： Cross-coupling Umpolung domino reactions Enaminone Benzofurans 2,3-Dihydrobenzofurans

Sequence [2,3]-Sigmatropic Rearrangement: One-Pot Synthesis of Proparggyl Allenylamines

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Chinese Journal of Chemistry 2024年第18期42卷 2223-2227页

作者： Huihui Feng Yujuan Xie Lliang Huang Yongqing Xu Junhai Huang Huangdi Feng College of Chemistry and Chemical Engineering Shanghai University of Engineering ScienceShanghai 201620China Shanghai Frontiers Science Research Centerfor Druggability of Cardiovascular noncoding RNA Institute for Frontier Medical Technology Shanghai Universityof Engineering ScienceShanghai 201620China

Allenes,served as highly sought-after building blocks,are an indispensable component of synthetic *** utility in modulating the chemical,physical,and pharmaceutical properties of organic compounds make allenes a desirable choice in various ***,we report a facile method for the atom-economical synthesis of propargyl allenylamines via an underdeveloped[2,3]-sigmatropic *** strategy employs easily accessible propargylamines as starting materials,which are first converted into propargyl ammonium salts,followed by a base-promoted[2,3]-sigmatropic *** one-pot,two-step reaction proceeds in the absence of transition metals,displays a very broad scope,and does not require the introduction of the electron-withdrawing group into the starting materials.

关键词： Allene Propargylamine C-N activation Sigmatropic rearrangement Metal-free Synthetic methods domino reactions

A Highly Diastereoselective Three-component domino Reac- tion in Water Yielding Poly-substituted 4,5-Dihydropyrroles

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Chinese Journal of Chemistry 2013年第8期31卷 1039-1044页

作者： Guangjing Tong Haiwei Xu Wei Fan Bo Jiang Shuliang Wang Shujiang Tu School of Chemistry and Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials Jiangsu Normal University Xuzhou Jiangsu 211116 China Jiangsu Provincial Xuzhou Pharmaceutical Vocational College Xuzhou Jiangsu 221116 China

An efficient methodology for highly diastereoselective synthesis ofpoly-substituted 4,5-dihydropyrrole deriva- tives from readily available common reactants in water has been developed. During domino processes, the forma- tion of pyrrole skeleton and its C2-hydroxylation and C3-arylamination were readily achieved via metal-free [3 ＋2] heterocyclization in a one-pot operation.

关键词： highly diastereoselective 4,5-dihydropyrroles hydroxylation arylamination domino reactions

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

Engaging Yne-Allenes in Cycloaddition reactions: Recent Developments

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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 *** yne-allenes in numerous annulation cascades provides efficient and direct accesses to elaborate functionalized polycyclic molecular architectures in a convergent *** 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 *** 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

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 *** alkyne hydroamination is a powerful method for the construction of *** the last two decades,copper-catalyzed domino reactions based on intramolecular alkyne hydroamination has emerged as a robust strategy for assembling various fused polycyclic *** progress has been achieved in 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 *** 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