Three-Component One-Pot Synthesis of Polyhydroacrodine Derivatives in Aqueous Media

9,10-Diaryldecahydroacridine-1,8-diones were synthesized by a three-component reaction of aromatic aldehydes, aromatic amines, and 5,5-dimethyl-1,3-cyclohexanedione using sodium 1-dodecanesulfonic (SDS) as the catalyst in aqueous media. The key intermediates before the cyclization step were obtained and characterized. The structures of all the products were determined by IR and ¹H NMR spectra and further confirmed by single-crystal x-ray diffraction analysis.     

水中3,3,6,6-四甲基-9-芳基-1, 8-二氧代-1,2,3,4,5,6,7,8-八氢化氧杂蒽的合成

以氨基磺酸和十二烷醇硫酸钠(SDS)为复合催化剂, 芳醛和5,5-二甲基-1,3-环己二酮为原料, 于水中合成了3,3,6,6- 四甲基-9-芳基-1,8-二氧代-1,2,3,4,5,6,7,8-八氢化氧杂蒽. 方法具有操作简便, 催化剂价廉易得、活性高、对环境友好、可回收重复使用等优点.     

一锅法合成新型异吲哚啉酮衍生物

以二价铜为催化剂,邻溴苯甲酸、苯乙炔和伯胺为原料,经一锅法合成了12个以异吲哚啉酮为母核的新化合物,其结构经¹H NMR, ¹³C NMR 和HR-MS(ESI)表征。并对催化机理进行了探讨。     

氯化铜催化三组分“一锅法”合成新型N1-取代3,4-二氢嘧啶酮衍生物

以二水合氯化铜为催化剂,通过等摩尔芳香醛、乙酰乙酸甲(乙)酯和N-取代脲的Biginelli缩合反应,"一锅法"合成了19个N1-取代的3,4-二氢嘧啶酮衍生物,其中11个为新化合物,其结构经~1H NMR,~(13)C NMR和MS表征。考察了催化剂用量和反应温度对产物收率的影响。结果表明最优反应条件为:催化剂用量为0.3mmol,反应温度为90℃。并对催化机理进行了探讨。     

超声辐射下水介质中一锅合成3-甲基-4-芳亚甲基-异噁唑-5(4H)-酮

报道了室温超声辐射下, 水相中通过乙酰乙酸甲酯、盐酸羟胺和芳香醛的三组分一锅反应, 合成了一系列3-甲基-4-芳亚甲基-异噁唑-5(4H)-酮衍生物. 在超声波辐射下, 参与反应的醛无论芳环上连有吸电子基或供电子基, 该一锅反应在室温下都能较好地进行; 对于α,β-不饱和醛、杂环芳醛以及二元芳醛与乙酰乙酸甲酯、盐酸羟胺的一锅反应也能在室温下顺利进行, 获得中等以上的收率. 产物的结构通过元素分析, IR, 1H NMR及单晶解析表征. 该方法具有操作简单和环境友好等优点.     

水介质中9,10-二芳基吖啶的洁净合成

水介质中在十二烷基磺酸钠(SDS)催化下, 席夫碱与双甲酮反应合成了一系列9,10-二芳基吖啶衍生物, 同时分离得到一种中间产物. 所有产物的结构通过红外光谱和1H NMR光谱确定, 产物10-(4-氯苯基)-9-(4-甲氧基苯基)-3,3,6,6-四甲基-3,4,6,7,9,10-六氢化吖啶-1,8(2H,5H)-二酮(3i)和中间产物2-{4-氯苯基-[2-(4-甲氧基苯基氨基)-4,4-二甲基-6-氧代环已-1-烯基]甲基}-3-羟基-5,5-二甲基环已-2-烯酮(4h)的结构还通过单晶X射线衍射分析确证.     

超声辐射下水介质中三组分一锅合成吡喃并[2,3-d]嘧啶衍生物

报道了在超声波辐射下, 水相中无催化剂下通过芳香醛与丙二腈、巴比妥酸的一锅反应, 合成了一系列吡喃并[2,3-d]嘧啶衍生物. 在超声波辐射下, 不仅饱和芳香醛与丙二腈、巴比妥酸的一锅反应在室温下能高收率地进行, 而对于α,β-不饱和醛以及二元醛与丙二腈、巴比妥酸的一锅反应也能在室温下顺利进行, 获得较高的收率. 产物的结构通过IR, 1H NMR和元素分析表征. 该方法具有操作简单和环境友好等优点.     

Efficient Synthesis of 3-Pyrrolin-2-one Derivatives in Aqueous Media

An efficient one-pot, three-component synthesis of 3-pyrrolin-2-ones in aqueous media at room temperature is reported. This reaction provides a green and catalyst-free method for generation of 3-pyrrolin-2-one derivatives in good yields.     

水介质中吡喃并[3,2-c]吡喃-5-酮衍生物的三组分一锅合成

水介质中在氯化三乙基苄基铵(TEBAC)催化下, 芳醛与丙二腈和4-羟基-6-甲基吡喃-2-酮三组分一锅反应合成了一系列2-氨基-3-氰基-4-芳基-4H,5H-吡喃-5-酮. 该反应具有产率高、污染少、操作简单、环境友好等优点.     

水介质中1,6-二氧-5-氧代-1,4,5,6-四氢化菲衍生物的三组分一锅合成

水介质中在氯化三乙基苄基铵(TEBA)催化下, 芳醛与丙二腈和4-羟基香豆素三组分一锅反应合成了2-氨基-4-芳基-3-氰基-1,6-二氧-5-氧代-1,4,5,6-四氢化菲, 该反应具有产率高、污染少、操作简单、环境友好等优点.     

水介质中4-芳基-3-甲基-1-苯基-4,5,6,7,8,9-六氢化吡唑并[5,4-b]喹啉-5-酮衍生物的三组分一锅合成

在水介质中有十二烷基磺酸钠(SDS)存在下, 以芳醛、5-氨基-3-甲基-1-苯基吡唑、1,3-环己二酮三组分一锅反应合成了4-芳基-3-甲基-1-苯基-4,5,6,7,8,9-六氢化吡唑并[5,4-b]喹啉-5-酮衍生物, 产物的结构通过IR, ¹H NMR确证, 化合物4e的结构经单晶X射线衍射确证.     

Facile Synthesis of Bibenzyl by Reductive Homocoupling of Benzyl Halides in Aqueous Media

A facile synthesis of bibenzyl derivatives by reductive homocoupling reaction is described. Treatment of benzyl halides with metallic iron powder in the presence of a catalytic amount of cuprous salt in aqueous media gives bibenzyls in good yields.     

A Facile and Clean Synthesis of Pyrimidine Derivatives via Three-component Reaction in Aqueous Media

A series of 5‐benzylidenepyrimidine‐2,4,6(1H,3H,5H)‐trione and 5,5′‐(arylmethylene) bis[6‐aminopyrimidine‐ 2,4(1H,3H)‐dione] derivatives were synthesized via the three‐component reactions of aromatic aldehyde, 6‐aminopyrimidine‐2,4‐dione and Medrum's acid in aqueous media in the presence of triethylbenzylammonium chloride. The structures of the products were affected by substituents of aromatic aldehydes.     

Synthesis of 7-Hydroxyspiropyran

The 7-acetoxyspiropyrans (4a and 4b) have been prepared by the reaction of Fischer's bases (3) with 2,4-diacetoxybenzaldehyde in refluxing ethanol in moderate yields. The acetyl group of 7-acetoxy-spiropyran 4a was easily removed to give a 7-hydroxyspiropyran 6 in high yield under the basic condition.     

On The Nature of FeIV=Oaq in Aqueous Media: A DFT analysis

Fe^IV=O_aq is a key intermediate in many advanced oxidation processes and probably in biological systems. It is usually referred to as Fe^IV=O²⁺. The pKa's of Fe^IV=O_aq as derived by DFT are: pKa1=2.37 M06 L/6-311++G(d,p) (SDD for Fe) and pKa2=7.79 M06 L/6-311++G(d,p) (SDD for Fe). This means that in neutral solutions, Fe^IV=O_aq is a mixture of (H₂O)₄(OH)Fe^IV=O⁺ and (H₂O)₂(OH)₂Fe^IV=O. The oxidation potential of Fe^IV=O_aq in an acidic solution, E⁰{(H₂O)₅Fe^IV=O²⁺/Fe^III(H₂O)₆³⁺, pH 0.0} is calculated with and without a second solvation sphere and the recommended value is between 2.86 V (B3LYP/Def2-TZVP, with a second solvation sphere) and 2.23 V (M06 L/Def2-TZVP without a second solvation sphere). This means that Fe^IV=O_aq is the strongest oxidizing agent formed in systems involving Fe^VIO₄²⁻ even in neutral media.     

水介质中微波促进一锅法合成吡喃并[2,3-d]嘧啶衍生物

水相中将芳香醛、丙二腈和巴比妥酸以等摩尔比混合,微波辐射5~15 min,合成了9种7-氨基-6-氰基-5-芳基吡喃并[2,3-d]嘧啶二酮,产率为80%~92%,避免了传统合成法反应时间长和中间体分离的繁琐操作,减少了环境污染。 产物结构通过IR、¹H NMR和元素分析测试技术进行了表征。     

Efficient One-pot Synthesis of 12-Aryl-8, 9, 10, 12-tetrahydrobenzo[a]xanthen-11-ones Under Solvent-free Conditions

Multi-component condensation of 2-naphthol, aromatic aldehydes, and cyclic 1,3-dicarbonyl compounds catalyzed by ionic liquid [NSPTEA][HSO₄] was accomplished for the synthesis of a series of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones under solvent-free conditions. High yields, ease recovery, short reaction time and reusability of catalyst are significant advantages. ZrOCl₂·8H₂O was also found to act as an effective catalyst towards this transformation.     

Synthesis and Properties of Alkylene (Dialkyl) Dithiophosphate Derivatives of Thionyl Chloride

Alkylene (dialkyl) dithiophosphate derivatives of thionyl chloride of the general formula (S)SS(O)Cl and (RO)₂(S)SS(O)Cl where G = ─ CH₂(CH₃)₂CCH₂─, ─ CH₂CH₂CH(CH₃)─, ─ C(CH₃)₂CH₂CH(CH₃)─ and R = i-C₃H₇, have been synthesized by reacting thionyl chloride with alkylene/dialkyl dithiophosphates in a 1:1 molar ratio in refluxing benzene. A similar reaction in a 1:2 molar ratio yields the corresponding products of the type (S₂)₂S═O and [(RO))₂PS₂]₂S═O. It is interesting to note here that the sulfur atom of the thionyl chloride has been retained in the product, which is evidenced by sulfur analysis. The products thus obtained are light yellow colored semi solid (1:1 products) and orange colored liquids (1:2 products); and are soluble in common organic solvents. These new compounds have been characterized by elemental analysis, molecular weight measurements, and spectroscopic [IR and NMR (¹H and ³¹P)] studies. These compounds are found to be biologically active against bacteria S.aureus and E.coli.     

Facile and Clean Synthesis of Furopyridine Derivatives via Three-Component Reaction in Aqueous Media Without Catalyst

A series of furo[2′,1′:5,6]pyrido[2,3-d]pyrimidine derivatives were synthesized via the three-component reaction of an aldehyde, tetronic acid, and 6-amino-1,3-dimethyl-pyrimidine-2,4-dione in aqueous media without the use of catalyst. This protocol has the advantages of better yields, less cost, reduced environmental impact, and convenient procedure.     

邻甲基苯磺酸铜催化"一锅法"合成3,4-二氢嘧啶-2(1H)-酮

二氢嘧啶酮(DHPMs)及其衍生物具有广泛的生物活性,如抗病毒、抗肿瘤、抗癌、抗高血压及消炎等作用[1].此外,DHPMs及其衍生物作为钙通道阻滞剂、α1a-对抗剂和神经肽Y的对抗剂,显示出良好的药理活性[2].更重要的是,最近几种含二氢嘧啶酮-5-羧酸盐的海洋生物碱被成功分离出来,并表现出重要的生物学性质[3],某些可以阻止HIVgp-120-CD4键的形成,是一种潜在的HIV抑制剂[4].因此,对DHPMs及其衍生物的研究成为生物活性有机杂环化合物的研究热点之一.