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Cobalt-Catalyzed Switchable[4+1]and[4+1+1]Spirocyclization of Aromatic Amides with 2-Diazo-1H-indene-1,3(2H)-dione:Access to Spiro Indene-2,1'-isoindolinones and Spiro Isochroman-3,1'-isoindolinones

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Chinese Journal of Chemistry 2024年第4期42卷 363-369页

作者： Bin Li Mengmeng Xie Jingyu Li Nana Shen Xinying Zhang xuesen fan State Key Laboratory of Antiviral Drugs Pingyuan LaboratoryKey Laboratory of Green Chemical Media and ReactionsKey Laboratory for Yellow River and Huai River Water Environmental Pollution ControlMinistry of EducationSchool of EnvironmentSchool of Chemistry and Chemical EngineeringHenan Normal UniversityXinxiangHenan453007 China

Herein,we report a condition-controlled divergent synthesis of spiro indene-2,1'-isoindolinones and spiro isochroman-3,1'-isoindolinones through cobalt-catalyzed formal[4+1]and[4+1+1]spirocyclization of aromatic amides with 2-diazo-1H-indene-1,3(2H)-dione.When the reaction is carried out under air in ethyl acetate,spiro indene-2,1'-isoindolinones are formed through Co(II)-catalyzed C—H/N—H[4+1]spirocyclization.When the reaction is run under O2 in CH3CN,on the other hand,spiro isochroman-3,1'-isoindolinones are generated through Baeyer-Villiger oxidation of the in situ formed spiro indene-2,1'-isoindolinones with O2 as a cheaper and environmental-friendly oxygen source.In general,these protocols have advantages such as using non-precious and earth-abundant metal catalyst,no extra additive,high efficiency and regioselectivity.A gram-scale synthesis and the removal of the directing group further highlight its utility.

关键词： Spiro indene-2,1'-isoindolinones Spiro isochroman-3,1'-isoindolinones 3d Transition metals Cobalt-catalyzed C-H Activation Switchable[4+1]and[4+1+1]spirocyclization Aromatic amides 2-Diazo-1H-indene-1,3(2H)-dione

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Synthesis of spirocyclopropylpyrazole derivatives via the cascade reaction of alkylidenecyclopropanes with pyrazolidinones and trifluoroethanol

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Organic Chemistry Frontiers 2022年第5期9卷 1410-1416页

作者： Mengyang Shen Yuanshuang Xu Xinying Zhang xuesen fan NMPA Key Laboratory for Research and Evaluation of Innovative Drug Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine ChemicalsKey Laboratory of Green Chemical Media and ReactionsMinistry of EducationSchool of Chemistry and Chemical EngineeringHenan Normal UniversityXinxiangHenan 453007China

A novel synthesis of spirocyclopropylpyrazole derivatives tethered with a trifluoromethyl unit through an unprecedented cascade reaction of alkylidenecyclopropanes with pyrazolidinones and trifluoroethanol(TFE)has bee... 详细信息

关键词： alkyl ethanol spiro

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Selenium-catalyzed oxidative carbonylation of 1,2,3-thiadiazol-5-amine with amines to 1,2,3-thiadiazol-5-ylureas

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Chinese Chemical Letters 2019年第2期30卷 375-378页

作者： Xiaopeng Zhang Shuxiang Dong Qianqian Ding xuesen fan Guisheng Zhang Henan Key Laboratory of Organic Functional Molecules and Drug Innovation Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals Key Laboratory of Green Chemical Media and Reactions Ministry of Education School of Chemistry and Chemical Engineering Henan Normal University

A facile one-pot, economical approach to 1,2,3-thiadiazol-5-ylureas was developed via seleniumcatalyzed oxidative carbonylation of 1,2,3-thiadiazol-5-amine with a series of amines in one-pot manner in the presence of CO and O_2. This approach is featured with cheap and easily available raw materials,cheap and reusable catalyst selenium, one-pot procedure, high atomic economy, simple operations and no emission of corrosive wastes.

关键词： Selenium Oxidative carbonylation 1,2,3-Thiadiazol-5-amine 1,2,3-Thiadiazol-5-ylureas Phase-transfer catalysis

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Synthesis of Chromeno[4',3':4,5]imidazo[1,2-α]pyridin-6-ones via Cascade Reactions of 2-(2-Bromophenyl)imidazo[1,2-α]pyridines

Synthesis of Chromeno[4',3':4,5]imidazo[1,2-α]pyridin-6-one...

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河南省化学会2016年学术年会

作者： Ju Zhang Xinying Zhang xuesen fan Key Laboratory of Green Chemical Media and Reactions Ministry of Education School of Chemistry and Chemical Engineering Henan Normal University

Imidazopyridine compounds are important nitrogen-containing heterocycles existing widely in natural products, pharmaceuticals, pesticides, and dyes. In another aspect, chromenone derivatives are found to be endowed with antioxidant, anticancer, and HIV protease inhibiting activities.Therefore, the search for convenient and effective methods for the preparation of6H-chromeno[4’,3’:4,5]imidazo [1,2-α]pyridin-6-ones, a hybrid structure consisting both the imidazopyridine and the chromenone scaffolds, is an important task in synthetic chemistry.As a continuation of our recent interest in searching new synthetic methods for the preparation of imidazo[1,2-α]pyridines-related heterocycles, we have developed an efficient synthesis of6H-chromeno[4’,3’:4,5]imidazo[1,2-α]pyridin-6-ones by reacting 2-(2-bromophenyl)imidazo[1,2-α]pyridines with CO under the promotion of Pd catalyst in the presence of Cu(OAc)2(Scheme 1).The formation of the title compounds is believed to go through a cascade process consisting of acetoxylation, deacetylation, CO insertion and C-H bond activation. Notable features of this novel method include simple starting materials without prefunctionalization, sustainable oxidant, and high efficiency.

关键词： Imidazo[1,2-α]pyridines Chromenone Cascade reaction Carbonylation

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Selective access to 3-cyano-1H-indoles, 9H-pyrimido [4,5-b] indoles or 9H-pyrido [2,3-b] indoles through copper-catalyzed cascade reactions

Selective access to 3-cyano-1H-indoles, 9H-pyrimido [4,5-b] ...

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中国化学会第九届全国有机化学学术会议

作者： Bin Li Shenghai Guo Xinying Zhang xuesen fan School of Chemistry and Chemical Engineering Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals Key Laboratory of Green Chemical Media and Reactions Ministry of Education Henan Normal University

Indole and its derivatives are attracting tremendous attention owing to their wide range of medicinal activities,frequent occurrence in natural products and multiple uses in organic synthesis.1]So far,a number of synthetic strategies toward indole derivatives have been developed.2]While these pioneering methods are generally efficient and reliable,they usually start

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C(sp3)-H Dehydrogenation and C(sp2)-H Alkoxy Carbonylation of Inactivated Cyclic Amines towards Functionalized N-Heterocycles

C(sp3)-H Dehydrogenation and C(sp2)-H Alkoxy Carbonylation o...

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河南省化学会2018年学术年会

作者： Yan He fang Wang Xinying Zhang xuesen fan School of Environment School of Chemistry and Chemical EngineeringCollaborative Innovation Centre of Henan Province for Green Manufacturing of Fine ChemicalsKey Laboratory of Green Chemical Media and ReactionsMinistry of EducationHenan Normal University

Tetrahydropyridine(THP) and its derivatives are highly valuable in synthetic and medicinal chemistry since they are the essential structural motifs of numerous natural products, therapeutic agents and functional materials. Among them, THP-3-carboxylates are well known for their diverse biological activities such as anti-bacterial, antitubercular, M5 muscarinic receptor antagonizing, and α-glucosidase inhibiting. Due to their importance, several elegant methods for the preparation of THP-3-carboxylates have been developed, which include the reaction of N-benzyl γ-chloropropyl amines with conjugated alkynoates, phosphine-promoted [3+3] annulation of aziridines with allenoates, four-component reaction of primary amines with β-dicarbonyl compounds, α,β-unsaturated aldehydes and alcohols, etc. While these literature methods are generally reliable, regio-selective, efficient and atom-economy synthesis of THP-3-carboxylates from simple substrates under mild conditions still remains as a challenging topic in the synthetic chemistry arena.1-2 Herein, we wish to report a novel and efficient synthesis of THP-, DHP-or THA-3-carboxylates via the one-pot cascade reactions of piperidines, pyrrolidines or azepanes with CO and alcohols. Mechanistically, the formation of the target products involves firstly a dehydrogenation of saturated cyclic amines followed by an alkoxy carbonylation of the in situ formed cyclic enamine intermediates. In addition, the DHP-3-carboxylates thus obtained could readily undergo an oxidative aromatization to give the corresponding pyrrole-3-carboxy-lates by using O2 as a green oxidant. Compared with literature methods, the synthetic protocols developed herein have advantages such as readily available starting materials, practical reaction conditions, and multiple bond formation to give advanced structures in one pot with high atom-economy.

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Synthesis of pyrazolo[5,1-a]isoindoles and pyrazolo[5,1-a]isoindole-3-carboxamides through one-pot cascade reactions of 1-（2-bromophenyl） buta-2,3-dien-1-ones with isocyanide and hydrazine or acetohydrazide

Synthesis of pyrazolo[5,1-a]isoindoles and pyrazolo[5,1-a]is...

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中国化学会第九届全国有机化学学术会议

作者： Yan He Miaomiao Tian Xinying Zhang xuesen fan School of Chemistry and Chemical Engineering Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals Key Laboratory of Green Chemical Media and Reactions Ministry of Education Henan Normal University

＜正＞A novel and efficient method to construct the pyrazolo[5,1-a]isoindole scaffold1-3 via a one-pot three-component cascade reaction of 1-（2-bromophenyl）buta-2,3-dien-1-one with hydrazine and isocyanide promoted ...

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Synthesis of Benzocarbazoles via Rh(Ⅲ)-Catalyzed Cascade Reactions of 2-Arylindoles with α-Diazo Carbonyl Compounds

Synthesis of Benzocarbazoles via Rh(Ⅲ)-Catalyzed Cascade Re...

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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： Bin Li Beibei Zhang xuesen fan Xinying Zhang School of Chemistry and Chemical Engineering Henan Normal University

Benzo[a]carbazoles and their derivatives possess diverse biological activities and unique photographic properties.Due to their importance,a number of synthetic methods based on different annulation strategies have been developed.While these elegant methods are generally efficient and reliable,the search for new synthetic protocols starting from easily obtainable substrates and accomplished under mild reaction conditions to give benzo[a]carbazoles bearing an unprotected NH unit is still highly desirable.In recent years,transition metal-catalyzed inert C–H bond activation followed by C–C or C–heteroatom bond formation has emerged as an attractive strategy in organic synthesis as it avoids multi-step pre-activation of starting materials and minimizes the production of unwanted by-products.Encouraged by the advantages demonstrated by transition metal-catalyzed C-H bond functionalization,we have studied the reaction of 2-arylindoles withα-diazo carbonyl compounds under the catalysis of Rh(III)catalyst.From this reaction,a series of diversely substituted benzo[a]carbazoles were prepared with good efficiency.To our knowledge,this is the first example in which the NH unit of indoles is used as a directing group for C(sp)–H bond carbenoid insertion and annulation to give benzo[a]carbazole derivatives.Notably,this novel method features with easily obtainable substrates,good functional group tolerance,excellent regio-selectivity,and high atom-efficiency.

关键词： α-diazo carbonyl compounds 2-arylindoles benzo[a]carbazoles C-H activation

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Tandem Reactions of 2-Alkynylbenzonitriles

Tandem Reactions of 2-Alkynylbenzonitriles

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河南省化学会2014年学术年会

作者： Yan He Yuanyuan Wang Xinying Zhang xuesen fan School of Chemistry and Chemical Engineering Henan Normal University

Inspired by the versatile reactivity of zinc bromide complex ofβ-enamino ester formed via the reaction of Reformatsky reagent with nitriles,we have developed a new synthesis of1-aminonaphthalene-2-carboxylate(2)throu...

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Novel Synthesis of Pyrazolo[1,5-a]quinazolines through copper-catalyzed tandem reactions

Novel Synthesis of Pyrazolo[1,5-a]quinazolines through coppe...

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河南省化学会2014年学术年会

作者： Lin Gao Yunping Song Xinying Zhang xuesen fan School of Chemistry and Chemical Engineering Henan Normal University

Pyrazolo[1,5-a]quinazolines have been frequently found in medicinally interesting compounds which are being developed as potential anti-inflammatory,antiallergic,anti-parasitic agents,1polymerase-12 and topoisomerase ... 详细信息

关键词： Pyrazolo[1,5-a]quinazoline Copper catalysis Tandem reaction

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