Silica-bonded N-propyl sulfamic acid as an efficient recyclable catalyst for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones under heterogeneous conditions

Silica-bonded N-propyl sulfamic acid(SBNPSA) catalyzed one-pot three component Biginelli condensation of different substituted aromatic aldehydes with ethyl acetoacetate and urea/thoiurea to the respective 3,4-dihydropyrimidin-2-(1H)-ones and thiones in environment friendly procedure is described. The facile reaction conditions, simple isolation and purification procedures of this method make it a good option for the synthesis of dihydropyrimidinones.     

二氧化硅包覆NiFe_2O_4担载Preyssler杂多酸用于合成双(二氢嘧啶酮)苯和3,4-二氢嘧啶-2(1H)-酮（英文）

A novel magnetic acidic catalyst comprising Preyssler(H14[Na P5W30O110]) heteropoly acid support‐ed on silica coated nickel ferrite nanoparticles (Ni Fe2O4@Si O2) was prepared.The catalyst was characterized by Fourier transform infrared,scanning electron microscopy,transmission electron microscopy,X‐ray diffraction,energy dispersive spectrum,VSM and particle size neasurement.Its catalytic activity was investigated for the synthesis of bis(dihydropyrimidinone)benzene and 3,4‐dihydropyrimidin‐2(1H)‐ones derivatives by the Biginelli reaction.With the catalyst,the reac‐tions occurred in less than 1 h with good to excellent yields.More importantly,the catalyst was easily separated from the reaction mixture by an external magnet and reused at least five times without degradation in the activity.     

A highly enantioselective synthesis of 5- (ι-menthyloxy) -4-substituted-3-chloro-2(5H) -furanones

In this paper, stereocontrolled tandem Michael addition-elimination reaction of the novel chiral source, S-(ι-menthyloxy)-3,4-dichloro-2(5H)-furanone, with various thiols and amines has been investigated. A series of new enantiomerically pure compounds, 5-(ι-menthyloxy)-4-substituted-3-cnloro-2(5H)-furanones, were obtained in good yields with d. e.(?)98% under mild conditions.     

1-甲基-3,4-二苯基喹啉-2(1H)-酮的合成和结构表征

以N-甲基苯胺和苯丙炔酸为原料,经过缩合、亲电环化、偶联反应合成了1-甲基-3,4-二苯基喹啉-2(1H)-酮;利用核磁共振谱和气相色谱-质谱表征了产物的结构.结果表明,所用合成方法具有产率高、反应条件温和、操作简单等优点,目标产物的总产率达62.7%.     

Synthesis and Crystal Structure of 4-（4-Chlorophenyl）-6-methyl-5-methoxy-caronyl-3,4-dihydropyrimidin-2（H）-one

1 INTRODUCTION Biginelli reaction is a three-component condensa-tion of ethyl acetoacetate, benzaldehyde and urea forthe synthesis of 3,4-dihydropyrimidin-2(1H)-ones(Scheme 1). The reaction can be carried out in aone-pot fashion in alcohol solution in t…     

A facile synthesis of 2,3-dihydro-2-aryl-4（1H）-quinazolinones catalyzed by scandium（Ⅲ） triflate

2,3-Dihydro-2-aryl-4(1H)-quinazolinones were prepared in good yields via condensation of o-aminobenzamide with aldehydes promoted by a catalytic amount of Sc(OTf)_3 under mild conditions.     

Ca(NO3)2•4H2O-catalysed Biginelli Reaction: One-pot Synthesis of 1,2,3,4-Tetrahydropyrimidin-2-ones/pyrimidine-2-thiones under Solvent-free Conditions

The synthesis of 1,2,3,4-dihydropyrimidinone/thione derivatives was achieved in good to excellent yields using calcium(II) nitrate as catalyst to promote the Biginelli three-component condensation reaction from a diversity of aromatic aldehydes, β-keto compounds and urea or thiourea. The reaction was carried out under solvent-free conditions.     

Studies on Fragmentation Regularity of 5-Methoxycarbonyl-4-substit uted-6-methyl-3,4-dihydropyrimidin-2（1H）-ones by Time-of-flight Mass Spectrometry

The electron impact time-of-flight(TOF) mass spectra of the title compounds were studied to establish their fragmentation processes. With the high resolution of the TOF instrument, the exact mass for each fragment was determined. These data were used to infer the molecular formulas and the elemental compositions for all the molecular ions and fragments through software interpretation. By further applying the fragmentation regularity, the majority of ions were fully assigned. The main fragmentation pathways of the title compounds include the formation of molecular ions by the loss of R^1 groups in the 4-position and the ester groups in the 5-position. The formed ion can be further fragmented by the elimination of MeOH.     

可见光诱导玫瑰红催化喹喔啉-2(1H)-酮的C3-H烷基化反应

建立了一种简单、实用的光诱导一锅法高选择性N-甲基喹喔啉酮类化合物和苯乙酮类化合物合成一系列3-烷基化喹唑啉-2(1H)-酮类化合物的方法。该方法在室温条件下,以玫瑰红作为光催化剂,在18 W 460nm的蓝色LED下照射8 h,通过直接C3-H活化的方案,较好收率获得一系列相应的3-烷基化喹喔啉-2(1H)-酮类化合物,最高产率可达到76%。反应体系具有经济实用性和底物适用范围广的特点,为3-烷基化喹喔啉-2(1H)-酮类化合物类化合物的合成提供了一种简便经济的方法。     

4-羟基-2(1H)-吡啶酮-3-甲酰胺类冬青生菌素类似物的合成与生物活性

以反式-4-羟基肉桂酸为起始原料,经乙酰化、酰基叠氮、curtius重排、加成和环合等6步反应合成了4-羟基-2(1 H)-吡啶酮-3-甲酰胺类冬青生菌素类似物,总收率17%.随后用滤纸片扩散法对该化合物的抑菌性能进行了初步研究.实验表明,该化合物对于白色念珠菌具有较好的抑制作用,对于酵母菌抑制作用较弱,对大肠杆菌和金黄色葡萄球菌基本无抑制作用.     

可见光诱导的2-(苄基氨基)苯甲酰胺合成4(3H)-喹唑啉酮

发展了一种环境友好的可见光诱导的反应.该方法在简单、温和的反应条件下可以通过2-(苄基氨基)苯甲酰胺来高效合成4(3H)-喹唑啉酮化合物.不使用任何金属、光催化剂和其他添加剂,仅在室温下用blue LED照射,反应就可以顺利进行并高收率得到相应的喹唑啉酮化合物.该反应具有反应底物范围广、官能团兼容性好、操作简单等优点,...     

Fe（NO3）3-9H2O/Fe（HSO4）3： An efficient reagent system for the oxidation of alcohols,thiols and sulfides in the absence of solvent

Fe（NO3）3-9H2O/Fe（HSO4）3 was used as an efficient reagent system for the oxidation of alcohols to their corresponding carbonyl compounds. All reactions were performed in the absence of solvent in good to high yields. Under the same reaction conditions, thiols and sulfides were also converted to their corresponding disulfides and sulfoxides, respectively. 2007 Farhad Shirini. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.     

Efficient synthesis of 4（3H）-quinazolinones using a soluble polymeric support

4（3H）-Quinazolinones have been synthesized from poly（ethylene glycol） （PEG） supported aza-Wittig reaction. 2-Dialkylamino- 4（3H）-quinazolinones 6 were synthesized efficiently by reaction of secondary amine with PEG-supported carbodiimides 4, which were obtained from aza-Wittig reaction of PEG-supported iminophosphoranes 3 with isocyanates.     

5-烷氧基-4-环胺基-3-卤-2(5H)-呋喃酮的合成与表征

在氟化钾作用下,亲核试剂环状仲胺与5-烷氧基-3,4二卤-2(5H)-呋喃酮在室温下发生串联的迈克尔加成-消除反应,合成了17个新化合物.通过旋光度,UV-Vis,IR,1H NMR,13C NMR,MS,元素分析和X射线单晶衍射等表征方法,确定了目标化合物的化学结构和绝对构型.     

Crystal Structure and DFT Studies of a Triazole Derivative： 4- （ 2-Hydrobenzylideneamino ） -3- （ 1,2,4-triazol-4-ylmethyl） 1H-1, 2,4-triazole-5 （4H） -thione

A novel triazole derivative 4-(2-hydrobenzylideneamino)-3-(1,2,4-triazol-4-ylmethyl)-1H-1,2,4-triazole-5(4H)-thione(1) was synthesized and characterized using elemental analysis, FTIR, and 1H NMR, and its crystal structure was determined via X-ray single crystal diffraction analysis. Crystal data: monoclinic, P2(1)/c, a=0.83335(9) nm, b=1.49777(16) nm, c=1.14724(12) nm, β =107.990(2)°, D=1.470 Mg/m3, and Z=4. The geometries and the vibrational frequencies were determined using the density functional theory(DFT) method at the B3LYP/ 6-31G level. To demonstrate the accuracy of the reaction route of compound 1, one of the important intermediates was also tested using the same method. The structural parameters of the two compounds calculated using the DFT study are close to those of the crystals, and the harmonic vibrations of the two compounds computed via the DFT method are in good agreement with those in the observed IR spectral data. The thermodynamic properties of the title compound were calculated, and the compound shows a good structural stability at normal temperature. The test results of biological activities show that it has a certain bactericidal ability.     

Synthesis of Gingerenone C and 5-Hydroxy-1-(4′-hydroxy-3-methoxyphenyl)-7-(4′′-hydroxyphenyl)-3-heptanone

Diarylheptanoidsconstituteadistinctgroupofmetabolitesofnaturalplantcharacterizedbytwoaromaticringslinkedbyalinearsevenaliphaticchain.Therehavebeenfewreportsonthebiologicalactivitiesofdiarylheptanoids,mostofwhichappearingintheareasofanti-inflammatory,anti-oxidative,superoxidescavengingandanti-hepatotoxiceffects1,2.SomeofthemareusedastraditionalmedicineinAsia3.Compound1and2werefirstlyisolatedfromtherhizomesofZingiberofficalrespectively4,5.Sofarthesynthesisofthesetwocompoundshavenotbeenreportedy…     

氯化亚锡催化“一锅法”合成N1-取代的3,4-二氢嘧啶-2(1H)-酮

以芳香醛、乙酰乙酸乙酯(甲酯)、单取代脲为原料,氯化亚锡为催化剂,在无溶剂、80℃条件下,通过三组分"一锅法"合成了一系列N1-取代的3,4-二氢嘧啶-2(1H)-酮衍生物。考察了催化剂用量和反应温度对产品收率的影响。通过IR、~1H NMR、~(13)C NMR和元素分析对目标产物结构进行确证,提出了可能的催化作用机理。本文的合成方法具有催化剂活性高、廉价易得和反应时间短、条件温和、产率高、绿色环保等优点。     

Three New Zn(Ⅱ)/Cd(Ⅱ) Coordination Polymers Constructed with 2-Mercaptonicotinic Acid and 1,2-Di(4-pyridyl)ethylene: Syntheses and Structure Analysis

Three new Zn(Ⅱ)/Cd(Ⅱ) coordination polymers based on 2-mercaptonicotinic acid (H2mna) with 1,2-di(4-pyridyl)ethylene (dpe) introduced as a bridging ligand have been synthesized via hydrothermal method and structurally characterized by single-crystal X-ray diffraction as well as elemental analysis and IR. As reported in this paper, [Zn2(dpe)0.5(mna)2] (1) can be classified as a two-dimensional layer structure in which the 1D chain composed of Zn(Ⅱ) and mna ligands is bridged by dpe ligands, while the complex named [Zn4(dpe)4(mna)4] (2) is a tetra-nuclear cluster compound. These two compounds are further extended to three-dimensional structures by hydrogen bonds along with C-H…π and π…π interactions. Compound 3 with general formular [Cd2(dpe)0.5(mna)2]·H2O belongs to a three-dimensional porous structure in which the 2D metal layers formed by the coordination of Cd(Ⅱ) and mna ligands are connected with the bridging of dpe ligands.     

Synthesis of propyl O-(α-L-rhamnopyranosyl)-(1→3)-[2,4-di-O-(2s-methylbutyryl)-α-L-rhamno-pyranosyl]-(1→2)-(3-O-acetyl-β-D-glucopyranosyl)-(1→2)-β-D-fucopyranoside,the tetrasaccharide moiety of Tricolorin A

Propyl O-(α-L-rhamncpyranosyl)-(1→3)-[2,4-di-O-(2s-methylbutyryl)-α-L-rham-nopyranosyl]-(1→2)-(3-O-acetyl-β-D-glucopyranosyl)-(1→2)-β-D-fucopyranoside (1), the tetrasac-charide moiety of Tricolorin A, was synthesized in total 23 steps with a longest linear sequence of 10 steps, and overall yield of 3.7% from D-Glucose. The isomerization of the dioxolane-type berzyli-dene in the presence of NIS/AgOTf was observed. Tetrasaccharide 1 exhibited no activity against the cultured P388 cell as Tricolorin A did.     

Synthesis and Crystal Structure of α-（1,2,4-Triazol-1H-yl）-ρ-chloro Acetophenone, [ClC6H4COCH2（C2H2N3）]

1 INTRODUCTION Triazole nuclei appear frequently in the struc- tures of various natural products and biologically active compounds, notably thiamine (vitamin B), penicillins, antibiotics such as micrococcin[1], and many metabolic products of fungi and primitive marine animals, including 2-(aminoalky)triazole-4- carboxylic acids[2]. Numerous triazole derivatives exhibit pharmacological activity[3], e.g., 4-amino-N- (triazole-2-yl)benzenesulfonamide is a commercial drug. We report herein …