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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：曹銎 Fan Yang Jing Sun Ying Huang Chao-Guo Yan 扬州大学 College of Chemistry and Chemical Engineering Yangzhou University

The spirooxindole system is the core structure of a wide variety of medicinal agents and natural products with broad biological activities ranging from antitumor,antimicrobial,antiHIV and antipyretics *** a consequence,considerable interest exists in organic and pharmaceutical chemistry for the development of elegant synthetic methodologies for diverse spirooxindole *** [3+2] cycloaddition of azomethine ylides generated from the addition reaction of isatins with primary amines or α-amino acids has become one of the most convenient synthetic methods for various spirooxindole systems. When we investigated the three-component reactions of L-proline,isatins and methyl propiolate,we successfully found that besides giving the expected spiro[indoline-3,3’-pyrrolizines],some novel medium sized cyclic fused oxindole compounds were conveniently obtained.2 The multicomponent reaction of L-proline,isatins with excess of methyl propiolates in methanol unexpectedly afforded 2-(oxoindolin-3-ylidene)propylidene)pyrrolidin-1-yl)acrylates in good yields,and the products subse quently converted to unique nine-membered pyrrolo[1 ’,2’:1,9]azonino[6,5,4-cd]indoles in the presence of ***,the multicomponent reaction of L-proline,N-benzylisatins and excess alkyl propiolates in refluxing chloroform unprecedentedly resulted in eight-membered azocino[1,2-a]benzo[c][1,5]diazocines as the main *** reaction mechanism was believed containing the sequential 1,3-dipolar cycloaddition,addition of cyclic tertiary amine to excess of propiolate and fascinating ring opening as well as rearrangement *** N-substituent on isatins played a critical role in the different reaction patterns.

关键词： multicomponent reaction spirooxindoles polyhetereocycle propiolate diazocine

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Facile synthesis of poly(aroxycarbonyltriazole)s with aggregation-induced emission characteristics by metal-free click polymerization

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Science China Chemistry 2011年第4期54卷 611-616页

作者： LI HongKun MEI Ju WANG Jian ZHANG Shuang ZHAO QiuLi WEI Qiang QIN AnJun SUN JingZhi TANG Ben Zhong MOE Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and Engineering Zhejiang UniversityHangzhou 310027China Department of Chemistry The Hong Kong University of Science & TechnologyClear Water BayKowloonHong KongChina

Regioseletive 1,3-dipolar polycycloadditions of 4,4'-isopropylidenediphenyl dipropiolate (1) and tetraphenylethene (TPE)-containing diazides (2) are carried out in polar solvents such as DMF/toluene at a moderate temperature of 100℃ for 6 h,producing poly(aroxycarbonyltriazole)s (PACTs) P3 with high molecular weights (Mw up to 23900) and regioregularities (F1,4 up to ～90%) in high yields (up to ～99%).These metal-free click polymerizations can propagate smoothly in an open atmosphere without protection from oxygen and *** obtained polymers are soluble in common organic solvents and thermally stable at temperatures up to 375℃.Thanks to their contained TPE moieties,the PACTs show aggregation-induced emission and can serve as fluorescent chemosensors for superamplified detection of explosives.

关键词： aggregation-induced emission metal-free click polymerization propiolate chemosensor

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Synthesis of highly functionalized pyrroles from primary amines and activated acetylenes in water

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Chinese Chemical Letters 2012年第10期23卷 1119-1121页

作者： S.Zahra Sayyed-Alangi Zinatossadat Hossaini Faramarz Rostami-Charati Department of Chemistry Azadshahr BranchIslamic Azad UniversityAzadshahrIran Department of Chemistry Qaemshahr BranchIslamic Azad UniversityQaemshahrIran Department of Chemistry Faculty of ScienceGonbad Kavous UniversityP.O.Box 163Gonbadlran

Stable derivatives of pyrroles were prepared using multicomponent reactions of dialkyl acetylenedicarboxylate, primary amine and propiolate in the presence of N-methylimidazole in water at room temperature in good yie... 详细信息

关键词： propiolate Dialkyl acetylenedicarboxilates Multicomponent reactions N-methylimidazole

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One-pot Sequential Reaction for the Synthesis of Polysubstituted 3-（3-Nitro-2-phenylchroman-4-yl）-3-arylaminoacrylates

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Chinese Journal of Chemistry 2013年第12期31卷 1546-1550页

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

The one-pot sequential reaction of arylamines, methyl propiolate and 2-aryl-3-nitrochromenes without any catalyst in refluxing ethanol afforded the polysubstituted 3-（3-nitro-2-phenylchroman-4-yl）-3-arylaminoacrylates in good yields and with high diastereoselectivity. Reaction mechanism was believed involving the initial formation of β-enamino ester and sequential Michael addition.

关键词： chromene propiolate acrylate arylamine one-pot reaction diastereoselectivity

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