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Regioselective electrochemical radical cascade cyclization of internal alkynes to selenated and trifluoromethylated dihydropyran

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Science China Chemistry 2023年第11期66卷 3178-3185页

作者： Mingming Yu Tiantian Huang Lin Zhang Muhammad Shabbir Yuhan Gao Yi-Hung Chen Hong Yi Aiwen Lei The Institute for Advanced Studies(IAS) Wuhan UniversityWuhan 430072China National Research Center for Carbohydrate Synthesis Jiangxi Normal UniversityNanchang 330022China

Dihydropyran(DHP)compounds are not only found in natural products and bioactive molecules,but also serve as important precursors in organic synthesis.Nonetheless,traditional methods for the construction of such compounds are usually limited to disubstituted DHPs.To address this synthetic challenge,reported here is an efficient electrochemical strategy toward the selenated and trifluoromethylated DHP compounds.The reaction proceeded smoothly under mild electrolysis conditions.The broad substrate scope(>50 examples)and scalable synthesis demonstrated the complexity-building potential of the strategy.Initial mechanistic studies reveal that cyclization may involve a radical process.This protocol may promote the further development of diversified synthesis of multi-substituted dihydropyran.

关键词： electrochemical organic synthesis dihydropyran cascade cyclization selenylation trifluoromethylation

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Pd-catalyzed cascade cyclization of allenylethylene carbonates and indandiones: Synthesis of tetracyclic dihydrocyclopentaindenofuranone derivatives

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Chinese Chemical Letters 2023年第10期34卷 131-134页

作者： Yujie Dong Jun Liu Xing Gao Ting Pan Biming Mao Songcheng Yu Yongjun Wu Cheng Zhang Hongchao Guo Department of Chemistry and Innovation Center of Pesticide Research China Agricultural UniversityBeijing 100193China College of Public Health Zhengzhou UniversityZhengzhou 450001China

A palladium-catalyzed cascade cyclization of allenylethylene carbonates with 1,3-indandiones was developed, providing biologically interesting tetracyclic dihydrocyclopentaindenofuranone derivatives having three contiguous quaternary carbon centers in moderate to high yields with excellent diastereoselectivities. In this reaction, the allene moiety was fully fused into the cyclopentene ring.

关键词： Palladium Allenylethylene carbonates Indandiones cascade cyclization Decarboxylation

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Synthesis of Polysubstituted 1H-Pyrrolo[3,2-c]quinolines via I2/Mn(OAc)3-Promoted cascade cyclization from 4-Hydroxyquinolines with in situ Generated Enamines

Synthesis of Polysubstituted 1H-Pyrrolo[3,2-c]quinolines via...

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中国化学会第十四届全国有机合成化学学术研讨会

作者： Fei Yu Jichao Zeng Ze Zhang School of Biological and Chemical Engineering Anhui Polytechnic University

1H-Pyrrolo[3,2-c]quinoline moiety represents one of the most important N-heterocycles in biologically active and naturally occurring molecules,and have been widely applied in medicinal chemistry or pharmacology.Therefore,a great deal of efforts have been devoted for synthesis of elaborated and diverse 1H-Pyrrolo[3,2-c]quinoline derivatives.For currently available methods,they often involve special or expensive starting materials,preliminary preparation of some kind of intermediates or precursors,and employ noble-or heavy-metal catalysts.On the other hand,I and Mn(OAc)-promoted cascade cyclization has been growing as wide and powerful strategy towards construction of various heterocycles,including our recent work on synthesis of N-containing heterocyclic compounds such as polysubstituted pyrroles and pyridines. Herein,we present an efficient and straightforward protocol for facile synthesis of a series of polysubstituted 1H-pyrrolo[3,2-c]quinolines via I/Mn(OAc)-promoted cascade cyclization from4-hydroxyquinolines with in situ generated enamines.Starting materials 4-hydroxyquinolines were easily prepared from the corresponding anilines and ethyl acetoacetate.This protocol exhibits the advantages of one-pot work up,high chemoselectivity,good functional group tolerance,cheap mediator and easily available starting materials.

关键词： enamine 4-hydroxyquinoline cascade cyclization 1H-pyrrolo[3,2-c]quinoline

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Synthesis of medium-sized benzo[b]azocines and benzo[b]azonines by photoinduced 8-/9-endo sulfonyl-cyclization

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Science China Chemistry 2023年第8期66卷 2309-2316页

作者： Kai Sun Dongyang Zhao Quanxin Li Shaofei Ni Guangfan Zheng Qian Zhang College of Chemistry and Chemical Engineering Yantai UniversityYantai264005China College Department of Chemistry and Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province Shantou UniversityShantou515063China Department of Chemistry Northeast Normal UniversityChangchun130024China

An efficient photochemical radical sulfonyl cyclization of designed dienes to medium-sized benzo[b]azocines and benzo[b]azonines was developed.This chemoselective method provides new highly functionalized eight-and nine-membered N-heterocycles.Radical inhibition experiments,light on/off experiments,and apparent quantum efficiency calculations were used to clarify the radical mechanism.Density functional theory calculations enabled rationalization of the rate-determining step and observed chemoselectivity.Large-scale synthesis and derivatizations via epoxidation and convenient N-Ts deprotection showed the potential utility of this strategy.This photochemical method for synthesizing sulfonylbenzo[b]azocines and sulfonylbenzo[b]azonines with insertion of sulfur dioxide provides new sustainable routes for the synthesis of valuable medium-sized Nheterocycles.

关键词： photocatalysis medium-sized N-heterocycles radical cascade cyclization DFT study

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Total Syntheses of （-）-Lycopodine and （-）-Lycospidine A via Phosphoric Acid Promoted Alkyne Aza-Prins cyclization

Total Syntheses of （-）-Lycopodine and （-）-Lycospidine A ...

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中国化学会第十三届全国有机合成化学学术研讨会

作者： Xingang Xie Xuegong She State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical EngineeringLanzhou University

The Lycopodium alkaloids are a skeletally diverse and structurally complex family of natural products,comprising approximately 300 known compounds which are divided into four groups:lycopodine group,lycodine group,fawcettimine group,and phlegmarine group.Among them,lycopodine（1） is the archetypal member of lycopodine family which possesses the classic tetracyclic core skeleton.Lycopodine was originally isolated from Lycopodium complanatum L.by B?deker in 1881,and its natural congener dihydrolycopodine（2） was discovered in 1942 by Manske and Marion.In 2013,the first example of a C15 N Lycopodium alkaloid named Lycospidine A（3）,containing an unprecedented five-membered A-ring,was isolated from Lycopodium complanatum by Zhao and co-workers.Due to their fascinating polycyclic architectures and diverse biological activities,we developed a phosphoric acid promoted and highly stereocontrolled alkyne aza-Prins cyclization reaction to achieve the asymmetric total syntheses of lycopodine（1）,dihydrolycopodine（2） and lycospidine A（3）.

关键词： aza-Prins cascade cyclization lycopodium alkaloids

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A Simple and Efficient Synthesis of 3-Benzoylquinoline-4-carboxylate Derivatives:Reaction of N,N-Dimethyl enaminone and Isatin Catalyzed by TMSCl

A Simple and Efficient Synthesis of 3-Benzoylquinoline-4-car...

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中国化学会第十三届全国有机合成化学学术研讨会

作者： Zhou Pan Xu Hui Lu Ling-Ling Yu Fu-Chao Faculty of Life Science and Technology Kunming University of Science and Technology

Quinolines is an important structural unit which exists in natural products and biologically active molecules.Their biological activities include antibacterial,antitumor,antileishmanial,antifungal and the treatment of malaria.[1-2] Due to these diverse activities,the synthesis of quinoline derivatives has attracted increasing attention from synthetic and medicinal chemists.[3] Enaminones is versatile substrates in the synthesis of heterocyclic compounds,as they undergo cyclization in various cascade reactions.[4] Interestingly,substituted pyrroloquinolines can be obtained from the reaction of enaminones with isatins,[4 a-g] but less attention has been paid to investigate quinolines reaction of them.Herein,we report a trimethylchlorosilane（TMSCl）-catalyzed cascade cyclization between N,N-dimethyl enaminones and isatins,which proceeded smoothly the synthesis of quinolines in alcohol.With this simple procedure,structurally diverse quinoline compounds were rapidly obtained in good to excellent yields.

关键词： quinolines cascade cyclization N,N-dimethyl enaminones

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Direct Synthesis of Benzo[f]indazoles from Sulfonyl Hydrazines and 1,3-Enynes by Copper-Catalyzed Annulation

Direct Synthesis of Benzo[f]indazoles from Sulfonyl Hydrazin...

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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： Biao Yao 苗涛 Pinhua Li Lei Wang Department of Chemistry Huaibei Normal University 淮北师范大学

Indazole moiety is a privileged N-heterocyclic structure in medicinal chemistry due to its pronounced biological and therapeutic activities,and especially,tricyclic 1 H-benzo-indazole plays increasingly important role in drug discovery. In the past few decades,a number of impressive methods have been reported for the construction of indazole frameworks, yet synthetic protocols to benzo[f]indazole are severely scarce,which have hampered their biomedical applications.In our work,a novel and efficient strategy for the direct synthesis of benzo[f]indazoles via copper-catalyzed cascade reaction of sulfonyl hydrazides with 1,3-enynes under mild conditions has been developed.This method achieves the formation of two C-N bonds and one C-C bond in one pot,providing a series of benzo[f]indazoles in good yields with good functional group tolerance and remarkable regioselectivity.

关键词： cascade cyclization 1,4-arylmigration 1,3-enyne benzo[f]indazole sulfonyl hydrazine

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