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Efficient Synthesis of the Functionalized spiro[indoline-3,4＇-pyridine] via Four-component Reaction

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Chinese Journal of Chemistry 2012年第7期30卷 1548-1554页

作者：孙晶吴群张藜娟颜朝国 College of Chemistry&Chemical Engineering Yangzhou UniversityYangzhouJiangsu 225002China

An efficient synthetic procedure for the functionalized spiro[indoline-3,4＇-pyridine] was developed via the four-component reactions of arylamines, acetylenedicarboxylates, isatins and malononitrile with triethylamine as the base catalyst. The advantages of this reaction are using common starting material, mild reaction conditions, broad scope of reactants and operational simplicity.

关键词： spiro compound isatin multicomponent reaction electron-deficient alkyne 1,4-dihydropyridine

Molecular diversity of triphenylphosphine promoted reaction of electron-deficient alkynes and arylidene Meldrum acid(N,N’-dimethylbarbituric acid)

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Chinese Chemical Letters 2020年第5期31卷 1337-1341页

作者： Ying Han Hui Zheng Yuan-Yuan Zhang Chao-Guo Yan College of Chemistry&Chemical Engineering Yangzhou UniversityYangzhou 225002China

The three-component reaction of triphenylphosphine,dimethyl hex-2-en-4-ynedioate and arylidene N,N’-dimethylbarbituric acids in dry methylene dichloride at room temperature afforded trans-1,3-disubstituted 7,9-diazaspiro[4.5]dec-1-enes in good yields and with high ***,the similar three-component reaction with arylidene Meldrum acids resulted in a mixtures of cis/trans-1,2-disubstituted 7,9-dioxaspiro[4.5]***,the three-component reaction of triphenylphosphine,dimethyl but-2-ynedioate and arylidene Meldrum acids gave polysubstituted 5-(triphe nyl-λ~5-phosphanylidene)cyclopenta-1,3-die nes.A plausible reaction mechanism was proposed for the formation of various products with different regioselectivity and diastereoselectivity.

关键词： Phosphine Electron-deficient alkyne Meldrum acid Barbituric acid spiro compound

Efficient Synthesis of spiro[furan-3,3＇-indoline] Derivatives via Reactions of Pyridinium Salts with Isatinylidene Acetoacetates

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Chinese Journal of Chemistry 2013年第8期31卷 1054-1058页

作者： Zhenming Liu Jun Fang Chaoguo Yan Analysis and Test Center Yangzhou University Yangzhou Jiangsu 225002 China College of Chemistry & Chemical Engineering Yangzhou University Yangzhou Jiangsu 225002 China Email: Chaoguo Yan (cgyan@***)[*]College of Chemistry & Chemical Engineering Yangzhou University Yangzhou Jiangsu 225002 China

An efficient synthetic procedure for the functionalized spiro[furan-3,3＇-indoline] derivatives was successfully developed by domino reactions of N-phenacylpyridinium bromides or N-ethoxycarbonylmethylenepyridinium bro- mide with isatinylidene acetoacetate in the presence of triethylamine in ethanol at room temperature. The mecha- nism included sequential Michael addition of the in situ generated pyridinium ylide and intramolecular substitution of enolate.

关键词： spiro compound spiro[furan-3,3'-indoline] pyrdinium ylide dihydrofuran Michael addition dominoreaction

Molecular Diversity of Three-Component Reaction of β-Enamino Imide, Malononitrile and Cyclic α-Diketones

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Chinese Journal of Chemistry 2017年第9期35卷 1422-1430页

作者： Man Xiao Chaoguo Yan College of Chemistry & Chemical Engineering Yangzhou University Yangzhou Jiangsu 225002 China

The base promoted three-component reaction of β-enamino imide, malononitrile and various cyclic α-diketones in acetonitrile showed interesting molecular diversity. The reactions with acenaphthylene-1,2-dione and ninhydrin afforded functionalized spiro[indene-2,4＇-pyrrolo[3,4-b]pyridines] and spiro[acenaphthylene-1,4＇-pyrrolo[3,4-b]- pyridines] in good yields. The similar reaction of phenanthrene-9,10-dione resulted in the formation of the unexpected complex phenanthro[9＇, 10＇：4,5]furo[2,3-c]pyrrolo[3,4-b]pyrroles in satisfactory yields.

关键词： multicomponent reaction β-enamino imide spiro compound ninhydrin phenanthrene-9,10-dione

Convenient Synthesis of spiro[benzo[d]pyrrolo[2,1-b]thiazole- 3,2＇-indenes] Derivatives via Three-Component Reaction

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Chinese Journal of Chemistry 2016年第4期34卷 412-418页

作者： Guoliang Shen Jing Sun Chaoguo Yan College of Chemistry & Chemical Engineering Yangzhou University Yangzhou Jiangsu 225002 China

The three-component reaction of N-phenacylbenzothiazolium bromides, aromatic aldehydes and indane-l,3- dione in ethanol at room temperature in the presence of triethylamine as base afforded functionalized spiro[benzo- [d]pyrrolo[2,1-b]thiazole-3,2＇-indenes] in good yields and with high diastereoselectivity. The 1H NMR data and sin- gle crystal structure clearly indicated that the obtained spiro compounds predominately have one diastereoisomer.

关键词： multicomponent reaction nitrogen ylide spiro compound benzothiazole indan-1,3-dione

Synthesis of spiro compounds via three-component reaction of aldimines,electron-deficient alkynes and cyclic diketones

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Synthesis of spiro compounds via three-component reaction of...

Synthesis of a 1,2,7,8-Tetraoxa-spiro[5.5]undecane

中国化学会全国第十一届有机合成化学学术研讨会

作者： Jing Zhang Chao-Guo Yan College of Chemistry & Chemical Engineering Yangzhou University

In the past decades,the chemistry of Huisgen’s 1,4-dipoles,which can be generated in situ from addition reaction of nitrogen-containing heterocycles such as pyridine,isoquinoline,imidazole and benzothiazole to electron-deficient alkynes have attracted much attentions of organic chemists,especially from the advantage point of heterocyclic synthesis. Many elegant domino reactions reactions were successfully developed on the basis of the subsequent interception of the zwitterions with versatile nucleophilic and electrophilic ***,which have similar structural scaffold to nitrogen-containing heterocycles such as pyridine and isoquinoline,can also act as nucleophiles to react with electron-deficient alkynes to form Huisgen’s 1,*** have developed an interesting three-component reaction of α,β-unsaturated N-arylaldimines or aldimines with dialkyl acetylenedicarboxylates and *** reaction not only provides a convenient synthetic procedure for the preparation of structurally diverse 2’,3’-dihydrospiro[indoline-3,6’-[1,3]oxazines]-4’,5’-dicarboxyIates in high yields,but also opens a new potentially applications of the aldimines in organic synthetic *** cyclic diketones such as acenaphthenequinone,benzoquinone,naphthalene- 1,4-dione can be used in the reactions.

关键词： multicomponent reaction spiro compound electron-deficient alkyne

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Chinese Journal of Chemistry 2007年第9期25卷 1304-1308页

作者：张琦李云伍贻康 State Key Laboratory of Bio-Organic and Natural Products Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China

Synthesis of a new spiro organic peroxide is described. The peroxy bonds were incorporated into the substrate framework via an acid-catalyzed ketal exchange reaction using hydrogen peroxide as the source of peroxy linkage. The hydroperoxyl groups were then bonded at the OH ends via Hg（II）-induced electrophilic additions to the C-C double bonds, giving a novel sprio structure with one peroxy bond in each of the two six-membered rings. The ester functionalities in the side chains also make it possible to conduct further structural modifications.

关键词： peroxide antimalarial artemisinin hydrogen peroxide spiro compound

Theoretical Studies on Aromaticity of spiro Metallaaromatics of （CloH10M）^2-（M=Ni, Pd, Pt）

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Chemical Research in Chinese Universities 2018年第3期34卷 470-474页

作者： LIU Nannan WANG Jian Chemistry Center College of Food Engineering Harbin University of Commerce Harbin 150076 R R. China Institute of Theoretical Chemistry Jilin University Changehun 130021 R R. China

Aiming to identify the spiro metallaaromatic systems with potential application value, （C10H10M）2 （M=Ni, Pd, Pt） derivatives were theoretically investigated. （C10H10M）^2 -Isol, which has two 6-membered rings（6MRs） connected by the M spiro atom, is a 14π-aromatic as a whole plane. （CloH10M）2 -Iso2 has one 6π-aromatic 5MR and one 10π-aromatic 7MR connected by the spiro atom. The free （C10H10M）^2- dianions could not exist due to their rather high frontier orbital energies, while the neutral （C10H10M）Li2 compounds are extremely stable against dissociation. Since （C10H10M）Liz coumponds axe not fully coordinated, they trend to form （C10H10M）Li4^2＋ dications, or even [（C10H10M）Li2]n polymers. Arguably, （C10H10M）^2- planes are not the only examples for spiro metallaaromaticity, their derivatives are also potential material building blocks.

关键词： Metalloaromaticity Metallabenzene spiro compound Inverse sandwich Through-space NMR shielding(TSNMRS)

Construction of Diverse Heterocycles via Cycloaddition of Heteroaromatic N-ylides and 2-Arylidene-1,3-indanediones

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Construction of Diverse Heterocycles via Cycloaddition of He...