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三联吡啶的合成及其金属配合物研究进展1刖言配位化学早期是在无机化学基础上发展起来的一门边沿学科，如今，配位化学在有机 化学与无机化学的交叉领域受到化学家门广泛的关注。
有机-金属配合物在气体分离、选择 性催化、药物运输和生物成像等方面都有潜在的应用前景，因此日益成为化学研究的热点 领域［1-4］。
多联吡啶金属配合物在现代配位化学中占据着不可或缺的位置，常见的多联吡 啶配体包括2,2'-二联吡啶（bpy ）和2,2':6'2'-三联吡啶（tpy ）（Fig. 1），Hosseini 就把bpy 称为“最广泛应用的配体” ［5］，与其类似的具有三配位点的tpy 的合成及其金属配合物的 研究同样是化学家们研究的热点［6-8］。
Fig 1.三联吡啶的三个吡啶环形成一个大的共轭体系，具有很强的 （7给电子能力，配合物中存在金属到配体的d 一 n *反馈成键作用，因而能与大多数金属离子均形成稳定结构的配 合物。
然而，三联吡啶金属络合物的特殊的氧化还原和光物理性质受其取代基电子效应的 影响。
因此，通过引入不同的取代基，三联吡啶金属络合物可用于荧光发光装置以及光电 开关等光化学领域［9-10］。
在临床医学和生物化学领域中，不管是有色金属的测定还是作 为DNA 的螯合试剂，三联吡啶衍生物都具有非常广泛的应用前景 ［11-12］。
2三联吡啶的合成研究进展正因为三联吡啶在许多领域都具有潜在的应用价值，所以对其合成方法的研究十分重 要。
三联吡啶的合成由来已久，早在 1932年，Morgan 就首次用吡啶在FeCR 存在下反应合成分离出了三联吡啶，并发现了三联吡啶与Fe （ II ）的配合物［13］。
目前，合成三联吡啶terpyridine tpy的方法主要有成环法和交叉偶联法两种。
2.1成环法成环法中最常用的反应是Kr? hnke 缩合反应( Scheme 1)[14]，首先2-乙酰基吡啶溴化得到化合物2, 2与吡啶反应生成吡啶溴盐3, 3与a 3■不饱和酮4进行Michael加成反应得到二酮5，在醋酸铵存在下进而关环得到三联吡啶。
CHEMICAL INDUSTRY AND ENGINEERING PROGRESS 2017年第36卷第9期·3300·化 工 进展离子液体催化二氧化碳合成环状碳酸酯的研究进展杨美1，钟向宏2，陈群3（1中山大学化学与化学工程学院，广东 广州 510275；2中国石油化工股份有限公司茂名分公司研究院，广东茂名525011；3常州大学江苏省精细石油化工重点实验室，江苏 常州 213164）摘要：离子液体作为一种新型绿色环保介质，由于其结构可设计、稳定性高以及催化活性高等优点，使其在CO 2环加成反应的催化方面应用前景广阔。
本文综述了近年来离子液体催化CO 2与环氧化物的环加成反应制备环状碳酸酯的研究进展。
传统离子液体包括咪唑类、吡啶类、季铵盐季盐等离子液体，而功能化离子液体包括羟基功能化、羧基功能化等离子液体。
与传统离子液体相比，功能化离子液体具有更好的催化活性。
无机或有机材料负载的非均相离子液体催化剂报道较多，载体包括SiO 2、氧化石墨烯、聚合物等。
非均相催化剂具备易分离、可在固定反应器中连续反应等优点，更适应工业化生产。
指出了CO 2与环氧化合物反应制备环状碳酸酯过程中出现的催化剂活性低、反应条件苛刻等关键问题，因此寻求高选择性合成环状碳酸酯的环境友好的新型高效催化剂具有重要的学术意义和实用价值。
关键词：二氧化碳；环氧化合物；环状碳酸酯；离子液体中图分类号：O643.3 文献标志码：A 文章编号：1000–6613（2017）09–3300–09 DOI ：10.16085/j.issn.1000-6613.2017-0282Recent progress of the synthesis of cyclic carbonates from CO 2 andepoxides catalyzed by ionic liquidsYANG Mei 1，ZHONG Xianghong 2，CHEN Qun 3（1School of Chemistry and Chemical Engineering ，Sun Yat-Sen University ，Guangzhou 510275，Guangdong ，China ；2Research Institute of Maoming Branch Company ，SINOPEC ，Maoming 525011，Guangdong ，China ；3Jiangsu ProvinceKey Lab of Fine Petrochemical Engineering ，Changzhou University ，Changzhou 213164，Jiangsu ，China ）Abstract ：As a novel environment friendly media ，ionic liquids(ILs) have shown advantages in the catalysis of this cycloaddition reaction due to their structure designability ，high stability ，and high catalytic activity ，etc ．This review was mainly focus on the latest progress on the use of ILs as catalysts for the cycloaddition of CO 2 with epoxides. The conventional ILs contained imidazolium ，pyridine ，quaternary ammonium salt ，quaternary phosphonium salts and other ILs. The functionalized ILs included hydroxyl-functionalized ，carboxyl-functionalized and other ILs. Compared with conventional ILs ，functionalized ILs had much better catalytic performance. A series of inorganic or organic support immobilizing ILs catalysts had been developed. Their supports included mesoporous silica ，graphene oxide ，polymers ，etc . The chemical industry has always preferred to use a heterogeneous catalyst due to the ease of separation and the ability to use in a fixed-bed reactor. How to overcome the disadvantages of low activities ，difficulties in separation and tough reaction conditions is a key issue. It is of great academic significance and practical value to pursue the new and efficient catalyst for high selectivity synthesis of cyclic carbonates.Key words ：carbon dioxide ；epoxides ；cyclic carbonates ；ionic liquids界面化学。
第34卷第1期2021年2月Vol.34No.1Feb.2021投稿网址： 石油化工高等学校学报JOURNAL OF PETROCHEMICAL UNIVERSITIESV2O5/g⁃C3N4催化剂的制备及其模拟油中硫化物的脱除张豪，李秀萍，赵荣祥（辽宁石油化工大学石油化工学院，辽宁抚顺113001）摘要：以三聚氰胺、偏钒酸铵、硼酸为前驱体，通过煅烧法制备V2O5/g⁃C3N4催化剂。
采用XRD、FT⁃IR、XPS、SEM和BET等技术对催化剂的结构与形貌进行表征。
以V2O5/g⁃C3N4为催化剂，乙腈为萃取剂，H2O2为氧化剂对模拟油中二苯并噻吩（DBT）的脱除进行考察。
探究了反应温度、催化剂质量、萃取剂体积、n(H2O2)/n(S)以及不同硫化物等因素对脱硫效果的影响。
在模拟油体积为5.0mL、萃取剂乙腈体积为3.0mL、n(H2O2)/n(S)=8、催化剂质量为0.02g、反应温度为30℃和反应时间为60min的最佳条件下，DBT的脱除率达到91.9%，经过5次催化剂再生后脱硫率仍可以达到85.7%。
关键词：V2O5/g⁃C3N4；氧化脱硫；二苯并噻吩；三聚氰胺中图分类号：TE624文献标志码：A doi：10.3969/j.issn.1006⁃396X.2021.01.002Preparation of V2O5/g⁃C3N4Catalyst and Desulfurization Ability in Model OilZhang Hao，Li Xiuping，Zhao Rongxiang（School of Petrochemical Engineering，Liaoning Petrochemical University，Fushun Liaoning113001，China）Abstract:The V2O5/g⁃C3N4catalyst was prepared by calcination method,using melamine,ammonium metavanadate,boric acid as precursors and methanol as solvent.The structure and morphology of the catalyst were characterized by X⁃Ray Diffraction(XRD), Fourier transform infrared spectroscopy(FT⁃IR),X⁃ray photoelectron spectroscopy(XPS),scanning tunneling microscope(SEM) and brunauer⁃emmett⁃teller(BET).The desulfurization ability of dibenzothiophene(DBT)in model oil was investigated using V2O5/g⁃C3N4as catalyst,acetonitrile as extractant and H2O2as oxidant.The effects of reaction temperature,amount of catalyst and extractant,n(H2O2)/n(S)molar ratio,and different sulfides on desulfurization rate were investigated.Under the optimum conditions: 5.0mL model oil,3.0mL acetonitrile,n(H2O2)/n(DBT)=8,0.02g of catalyst,temperature was30℃and reaction time was60min, the desulfurization rate of DBT can reach91.9%,which can also keep at a higher value at85.7%after5times of catalyst regeneration. Keywords:V2O5/g⁃C3N4；Oxidative desulfurization；Dibenzothiophene(DBT)；Melamine随着汽车工业的迅速发展，燃料油燃烧产生的硫化物对环境的污染越来越严重[1⁃2]。
金属催化端炔与亚胺衍生物亲核加成制备炔丙基胺的研究进展成明;李伯刚【摘要】综述了端炔与C=N双键亲核加成制备炔丙基胺的合成方法的研究进展.其中包括醛亚胺的间接或直接偶联反应,烯胺的间接偶联反应,酮亚胺的间接或直接偶联反应等.参考文献30篇.%This paper reviews the research progress with 30 references for propargylamines synthesis through the metal-catalyzed coupling reactions of imines and alkynes, including aldimines indirect or direct coupling reactions, enamines indirect coupling reactions, ketoimines indirect or direct coupling reactions.【期刊名称】《合成化学》【年(卷),期】2012(020)001【总页数】6页(P1-6)【关键词】炔丙基胺;金属催化;偶联反应;综述【作者】成明;李伯刚【作者单位】中国科学院成都有机化学研究所,四川成都610041;中国科学院研究生院,北京100039;中国科学院成都生物研究所,四川成都610041【正文语种】中文【中图分类】O622;O622.6近年来，随着生命科学的蓬勃发展，含氮化合物引起了人们的极大兴趣。
在合成的这些含氮化合物中，炔丙基胺就是一类非常重要的合成中间体，被广泛应用于合成天然产物和一些具有一定生物活性的复杂分子。
炔丙基胺分子中的C≡C键可以很容易发生氢化反应，此法可以用来设计合成含有不同饱和侧链的α-氨基酸衍生物。
另外由于炔基的富电子特性，炔丙基胺化合物可以经历[3+2]或[4+2]环加成反应制备其它类型的非天然氨基酸衍生物(Scheme 1)[1～7]。
LaCl 3Á7H 2O as an Efficient Catalyst for One-Pot Synthesis of Highly Functionalized Piperidines via Multi-component Organic ReactionsBalijapalli Umamahesh •Venkatesan Sathesh •Gunasekar Ramachandran •Munusamy Sathishkumar •Kulatu SathiyanarayananReceived:5March 2012/Accepted:14April 2012/Published online:15May 2012ÓSpringer Science+Business Media,LLC 2012Abstract The three-component one-pot synthesis of highly functionalized piperidine derivatives was carried out by condensing 1,3-dicarbonyl compounds with aromatic aldehydes and aniline using a catalytic amount (10mol%)of LaCl 3Á7H 2O in methanol at room temperature.The main features of current protocol include easy work up,mild reaction conditions,good yields and high atom economy.Keywords One-pot condensation ÁLanthanum chloride heptahydrate ÁAza Diels–Alder reaction ÁKnoevenagel condensation ÁFunctionalized piperidines1IntroductionAs an important aspect of synthetic organic chemistry,multi-component organic reactions (MCRs)are among the most prosperity reaction classes.1,3-Dicarbonyl com-pounds are one of the most multifaceted reagents to be used in MCRs because of the high reactivity of enaminones in both keto and enol forms,which are very advantageous to construct useful bioactive heterocycles [1,2].MCRs offer a highly valuable synthetic protocol for the construction of highly complex molecules with minimum number of syn-thetic steps.Wu et al.[3]has described the synthesis of naphthyridine derivatives in which thirteen bonds werecleaved and twelve new bonds were constructed through one-pot cascade reaction,while only two molecules of H 2O were removed.In most of the situations a single product was obtained from three or more different,willingly available starting materials in an illustrious synthetic manner through MCRs [4].The beneficial effects of these MCRs over the conventional synthesis are shorter reaction time,eco friendliness,cost effectiveness,high atom econ-omy,inexpensive purification and no necessity for pro-tection and deprotection process [5,6].Recently,Lewis acids catalyzed Michael addition of Schiff base to enami-nones has attracted great attention of synthetic chemists [7,8].Poly functionalized piperidines are widely distributed in naturally occurring monocyclic and bicyclic alkaloids and synthetic drugs [9].A variety of structural features sur-rounded the naturally occurring and synthetically prepared piperidines,among them many exhibit significant biologi-cal properties including anti-HIV,anticancer,antimyco-bacterial,antimicrobial,antimalarial,antiinflammatory,antiinsecticidal and they are potent inhibitors for many biological systems [10–14].Much considerable efforts have been focused on the synthetic methods and some of the synthetic routes have been recommended for the syn-thesis of highly substituted piperidines essentially intra-molecular Mannich reaction [15],cyclohydrocarboxylation [16],aziridine ring expansion [17],radical cyclization [18],domino reaction [19],Diels–Alder reaction [20],imino Diels–Alder reaction [21]and domino imino-aldol-aza-Michael addition [22].Recently one-pot synthesis of these scaffolds has been achieved by employing InCl 3[23],bromodimethylsulfonium bromide [24],L -proline/TFA [25],tetrabutylammonium tribromide [26],molecular I 2[27],CAN [28],ZrOCl 2Á8H 2O [29],picric acid [30],thiourea dioxide (TUD)[31],BF 3-SiO 2[32],VCl 3[33]andElectronic supplementary material The online version of this article (doi:10.1007/s10562-012-0829-x )contains supplementary material,which is available to authorized users.B.Umamahesh ÁV.Sathesh ÁG.Ramachandran ÁM.Sathishkumar ÁK.Sathiyanarayanan (&)Chemistry Division,School of Advanced Sciences,VIT University,Vellore 632014,India e-mail:sathiya_kuna@Catal Lett (2012)142:895–900DOI 10.1007/s10562-012-0829-xBi(NO3)3Á5H2O[34]as efficient catalysts.The above deliberated methods have some disadvantages such as the use of expensive and excess amount of catalysts.Effica-cious new approaches for the preparation of chemically and biologically active complex molecules are of great signif-icance with simple mechanism and good selectivity.Nowadays lanthanides including lanthanum[35],cerium [36],samarium[37]and ytterbium[38]have been employed as efficient catalysts for a wide variety of syn-thetic reactions.Jun Lu et al.[39]has described an efficient one-pot synthesis of3,4-dihydropyrimidinones using lan-thanum chloride heptahydrate as catalyst from an aldehyde, b-keto ester and urea or thiourea in ethanol.In continuation of this,here we report the one-pot efficient synthesis of highly functionalized piperidines using10mol%of LaCl3Á7H2O as a catalyst in a three-component intramo-lecular aza Diels–Alder reaction.2Result and DiscussionFor the initial optimization of the reaction conditions and the identification of the suitable solvent and effective reaction conditions,ethyl acetoacetate,benzaldehyde,ani-line and10mol%of catalyst was selected as prototype. Among the chosen solvents MeOH was the best for the synthesis of tetrahydropyridines showed in Table1. Although acetonitrile,chloroform and dichloromethane allowed the reaction at a faster rate,the yield was less than that obtained using MeOH as solvent.THF and ethyl acetate gave low yields and no desired product was obtained with water.By screening a wide range of catalysts,we found out that the product5a could be obtained in good yields ranging from20to83%in different mole ratios of LaCl3Á7H2O(1,2,5,10and15mol%)and the results are summarized in Table2.Better yields were obtained up to 83%by carrying out the reaction using10mol%of LaCl3Á7H2O in MeOH as solvent.The reaction takes place efficiently in an open air system and it does not require any special apparatus like Schlenk system.When the reaction was carried out at reflux conditions,there was no signifi-cant change in yields and time(Entry16,Table2).Primary screening studies of a variety of catalysts also revealed that lanthanum oxide and silica chloride also act as catalyst. La2O3(10mol%)and silica chloride(10mol%)were employed as catalysts for the three-component reaction but moderate yields were obtained.Lower yields were obtained with the use of NH4OAc and ammonium molybdate.A wide range of aromatic aldehydes and amines were subjected to react with1,3-dicarbonyl compounds in the presence of catalytic amount of LaCl3Á7H2O and the results are summarized in Table3.A variety of aromatic alde-hydes possessing electron withdrawing and electron donating groups at different positions on the aromatic ring,Table1Initial solvent effect studies for synthesis of tetrahydro-pyridines with10mol%catalystEntry Solvent Catalyst Time(h)Yield(%)a1CH3CN LaCl3Á7H2O3742CH2Cl2LaCl3Á7H2O 2.5763CHCl3LaCl3Á7H2O3724EtOAc LaCl3Á7H2O10445MeOH LaCl3Á7H2O3836EtOH LaCl3Á7H2O4767i-PrOH LaCl3Á7H2O 6.5708THF LaCl3Á7H2O8599H2O LaCl3Á7H2O12Traces10MeOH SiO2Cl37111CH3CN SiO2Cl 4.56612CHCl3SiO2Cl474 Conditions:ethyl acetoacetate(0.5mmol),benzaldehyde(1mmol), aniline(1mmol)and10mol%LaCl3Á7H2O in5ml solvent,stirring in room temperaturea Isolated yields Table2Screening of catalysts for the one-pot synthesis of tetrahydropyridinesEntry Catalyst(mol%)Time(h)Yield(%)a1NH4OAc(10mol%)24462(NH4)6Mo7O24Á4H2O(10mol%)24323AlCl3(10mol%)24244Triethyl amine(10mol%)24Traces5Li2O3?L-proline(10?5mol%)24406Al2O3acidic(10mol%)24357Al2O3basic(10mol%)24298ZnCl2(10mol%)24419FeCl3(10mol%)243210La2O3(10mol%)186511SiO2Cl(10mol%) 3.56812LaCl3Á7H2O(1mol%) 3.52013LaCl3Á7H2O(2mol%) 3.53514LaCl3Á7H2O(5mol%)36215LaCl3Á7H2O(10mol%)38316LaCl3Á7H2O(10mol%)381b17LaCl3Á7H2O(15mol%)381 Conditions:ethyl acetoacetate(0.5mmol),benzaldehyde(1mmol), aniline(1mmol)and10mol%catalyst in methanol(5ml),stirring in room temperaturea Isolated yieldsb Isolated yield when the reaction was carried out under reflux conditions896 B.Umamahesh et al.were allowed to react with ethyl acetoacetate under stan-dard conditions affording substituted piperidine with good yields.Nitro group (at 3and 4positions)containing alde-hyde gave moderate yields with both ethyl acetoacetate and methyl acetoacetate due to stable imine formation.Likewise a variety of aromatic anilines possessing electron withdrawing and electron donating groups,were allowed to react with ethyl acetoacetate and aromatic aldehydes under standard conditions and results are summarized in Table 3.Similarly for getting piperidine moiety,we treated ethyl acetoacetate and aniline with different aliphatic aldehydes including formaldehyde,acetaldehyde,and propanalde-hyde under same reaction conditions.However,no desired compounds were formed in the reaction.This is due to the electron releasing nature of alkyl groups in aliphatic aldehydes.The reaction is shown in Scheme 1.All the synthesized products were characterized by FTIR,H 1NMR,C 13NMR and mass spectral analyses.The structures of 4a and 5a were determined by single crystal X-ray diffraction analysis shown in Fig.1and it can be concluded that the ring exists in trans form.The H 1NMR spectral analyses of compounds 4a–4j and 5a–5m reveal that N–H peak comes around 10.250–10.350ppm with the exception of 4b which comes around 9.80ppm.Proton present at the stereogenic center C-2(denoted by asterisk in Scheme 2)position comes at around 6.35–6.55ppm.Pro-ton present at the stereogenic center is shifted towards the deshielding region,when the electron donating groups are present at para position on aromatic aldehyde ring.This is further confirmed by H 1NMR spectra of compounds 5g–j.In compound 5g and 5h stereogenic proton comes next to two aromatic protons but in the case of 5i and 5j stereo-genic proton comes first followed by aromatic proton.The possible reaction mechanism for this three-compo-nent reaction is described in Scheme Cl 3Á7H 2O is Lewis acid,which serves as an acid catalyst for the con-struction of b -enaminone (6)formed by the reaction of ethyl acetoacetate with aniline and imine (7)which is formed in the reaction of benzaldehyde with aniline (Step 1).Benzaldehyde which is retained in the reaction mixture undergoes Knoevenagel condensation with b -enaminone leading to the formation of intermediate 8and reactive form 8a (Step 2).Due to the diene core present in inter-mediate 8a ,it proceeds towards an intramolecular aza Diels–Alder reaction with imine (serves as dienophile)which affords the expected piperidine (Step 3).Interme-diates 6and 7had earlier been isolated from similar reaction.Table 3LaCl 3Á7H 2O (10mol%)catalyzed one-pot synthesis of highly functionalized piperidines Entry R 1R 2R 34,5Time (h)Yield (%)a 1H H Me 4a 3.58022OMe H Me 4b 3.56833NO 2H Me 4c 57044CN H Me 4d 4.57854Br H Me 4e 58164NO 2H Me 4f 4.56274Me H Me 4g 3.58884MeO H Me 4h 4849H 4Cl Me 4i 3.584104F 4Cl Me 4j 952114Me 4Cl Me 4k 3.57912H H Et 5a 383132F H Et 5b 7.569143F H Et 5c 3.573153Br H Et 5d 570163NO 2H Et 5e 5.549173Me H Et 5f 4.566184Me H Et 5g 469194Et H Et 5h 4.567204F H Et 5i 3.577214Cl H Et 5j 3.58222H 4Cl Et 5k 480234Me 4Cl Et 5l 3.573244Et 4Cl Et 5m 4.56925H 4Me Et 5n 4.580264Me 4Me Et 5o 482274Cl 4Me Et 5p 577284Me4NO 2Et5q874Conditions:1,3-dicarbonyl compound (0.5mmol),aromatic aldehyde (1mmol),aniline(1mmol)and 10mol%LaCl 3Á7H 2O in 5ml MeOH,stirring in room temperatureaIsolatedyieldsScheme 1Reaction of 1,3-dicarbonyl compound,aniline with various aldehydes in the presence of LaCl 3Á7H 2OLaCl 3Á7H 2O as an Efficient Catalyst8973Experimental Section3.1General Procedure for the preparation of Methyl1,2,5,6-Tetrahydro-1,2,6-triphenyl-4-(phenylamino)pyridine-3-carboxylate (4a )A mixture of b -keto ester (1mmol),aniline (2mmol)and LaCl 3Á7H 2O (0.1mmol)in 5ml methanol was stirred at room temperature for 15min followed by the addition of aldehyde (2mmol)and stirring was continued for an appropriate time.The completion of the reaction was monitored by TLC.The solid product formed in reaction mixture was filtered,washed with methanol and recrystal-lized using ethanol and tetrahedrofuran (1:1ratio).If the product was in gel form,it was purified by silica gel column chromatography using hexane and ethyl acetate aseluant.Fig.1Crystal structures of 4a and5aScheme 2Three-component one-pot reaction leading to poly substituted piperidines898B.Umamahesh et al.White yellow solid;melting point:192–194°C:IR (KBr):3250,3024,2949,2867,1815,1661,1606,1504,1449,1375,1321,1245,1183,1070,978,920,748,646cm -1:H 1NMR (400MHz,CDCl3)TM ppm:2.78–2.74(d,J =14.8Hz,1H),2.89–2.84(dd,J =30.4,5.6Hz,1H),3.93(s,3H),5.15(s,1H),6.29–6.26(d,J =7.6Hz,2H), 6.45(s,1H), 6.53–6.51(d,J =8.4Hz,2H),6.61–6.58(t,J =7.2Hz,1H),7.33–7.03(m,15H),10.25(br s,1H,NH);C 13NMR (100MHz,CDCl3)TM ppm:33.6,51.0,55.1,58.2,97.9,112.9,116.2,125.8,125.9,126.4,126.4,126.6,127.2,128.3,128.7,128.9,128.9,137.8,142.7,143.9,146.9,156.3,168.6;4ConclusionIn conclusion,we have developed a one-pot three-com-ponent intramolecular aza Diels–Alder reaction of alde-hydes,aniline and 1,3-dicarbonyl compounds in the presence of 10mol%of LaCl 3Á7H 2O in MeOH as an efficient catalyst.The main feature of this 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