Rapid and Efficient Synthesis of 3,3-Di(1H-indol-3-yl)indolin-2-ones and 2,2-Di(1H-indol-3-yl)-2H-acenaphthen-1-ones Catalyzed by p-TSA

An efficient synthesis of 3,3-di(1H-indol-3-yl)indolin-2-ones and 2,2-di(1H-indol-3-yl)-2H-acenaphthen-1-ones via a reaction of various isatins or acenaphthenequinone with indoles in the presence of p-methylbenzene sulfonic acid (p-TSA) in CH₂Cl₂ at room temperature is described. The advantages of this method include good reaction yield, simple workup procedure, and mild reaction condition.     

HFIP-promoted catalyst-free cascade reactions for the synthesis of biologically relevant 3,3-di(indolyl)indolin-2-ones from indoles and isatins

The first HFIP-promoted catalyst-free cascade reactions for the synthesis of biologically relevant 3,3-di(indolyl)indolin-2-ones (27 examples, up to 98% yield) from readily available indoles and isatin derivatives are described. This protocol shows well tolerance of different functional groups and features mild reaction conditions such as short reaction time (∼ 1 h), no usage of catalyst, easy operation and product isolation. Of particular interest is the formation of two CC bonds and one all-carbon quaternary center. This protocol could serve as an alternative strategy to synthesize biologically important 3,3-di(indolyl)indolin-2-ones for biological testing.     

Facile synthesis of 3,3-di(heteroaryl)indolin-2-one derivatives catalyzed by ceric ammonium nitrate (CAN) under ultrasound irradiation

Ceric ammonium nitrate efficiently catalyzes the reaction of isatin with indoles under sonic waves to afford symmetrical 3,3-di(indolyl)indolin-2-ones in excellent yields, as well as the reaction of 3-hydroxy-3-indolylindolin-2-ones with indoles, pyrrole to afford the corresponding adducts in excellent yields, which provides an efficient route to the synthesis of symmetrical and unsymmetrical 3,3-di(indolyl)indolin-2-one derivatives, respectively.     

Highly Efficient Synthesis of Bis（indolyl）methanes Catalyzed by Sodium Tetrafluoroborate

Sodium tetrafluoroborate （NaBF4） was found to catalyze the electrophilic substitution reactions of indoles with aldehydes and ketones under solvent-free conditions to afford the corresponding bis（indolyl）methanes in high yields.     

Synthesis of Bis(indolyl) Methanes in Catalyst- and Solvent-Free Reaction

Efficient synthesis of bis(indolyl) methanes by the reaction of indoles with various carbonyl compounds in the absence of catalyst and solvent afforded the corresponding bis(indolyl) methanes in excellent yields.     

3-取代吲哚酮类化合物的合成及抗癌活性研究

设计合成了9种未见报道的3-取代吲哚酮类化合物, 所有目标化合物的结构经1H NMR, IR, MS, 元素分析表征确证. 初步的生物学活性研究结果表明, 此类化合物对HL-60细胞系的增殖具有一定的抑制作用.     

Synthesis of Pharmacologically Active Bis(indolyl) and Tris(indolyl) Derivatives Using Chlorotrimethylsilane

Chlorotrimethylsilane is found to be a comparatively fast and efficient catalyst for carrying out electrophilic substitution reactions of indoles with various aldehydes/ketones/triethylorthoformate, yielding excellent amount of bis(indolyl)methanes/tris(indolyl)methanes. The merits of this protocol are avoidance of any external energy source, minimal reaction time, simple and easy procedure and high yield under solvent free room temperature condition. The versatility of this method has been tested with various aldehydes/ketones and received satisfactory results.     

Highly Efficient Synthesis of Unsymmetrical 3,3′‐Bis(1H‐indol‐3‐yl)methanes in Water

A simple and practical approach for the preparation of unsymmetric bis(indolyl)methanes (BIMs) was realized by Lewis acid InBr₃‐catalyzed Friedel‐Crafts reaction of indoles with 3‐indolyl‐substituted phthalides in water.     

对甲苯磺酸催化三吲哚烷基化合物的合成

室温下,吲哚与3-吲哚甲醛在对甲苯磺酸的催化下高收率得到三吲哚烷基化合物,所有产物的结构经1H NMR,IR和HR-MS表征。     

TEMPO/CuI synergetic catalyzed oxidative cross-coupling of indoles with benzylamines: Synthesis of bis(indolyl)phenylmethanes

TEMPO/CuI was found to be an effective catalyst for the cross-coupling of indoles with benzylic amines affording the corresponding bis(indolyl)phenylmethanes under air atmosphere at room temperature in good to excellent yields. The efficiency, easy workup, simplicity, and chemoselectivity of this protocol provide a green and low-cost procedure for the synthesis of these compounds.     

蒙脱土负载碘催化合成双吲哚甲烷衍生物

以蒙脱土负载碘(MMT/I2)作催化剂,醛(1a~1g)与吲哚(2)反应合成双吲哚甲烷衍生物(3a~3g),其结构经1H NMR和IR确证。以3a的合成为例,研究了催化剂、溶剂、反应时间、温度和物料比r[n(1)∶n(2)]对3产率的影响。结果表明:在最佳合成条件(2 1 mmol,r=1.1∶2.0,10 mol%MMT/I2,乙腈1 m L,于25℃反应5min)下,3a~3g产率67.9%~96.2%。MMT/I2循环使用3次,3a产率78.6%。     

One-Pot Synthesis of Novel 2-(Thiazol-2-yl)-4,5-dihydropyridazin-3(2H)-one Derivatives Catalyzed by Activated KSF

A series of 2-(thiazol-2-yl)-4,5-dihydropyridazin-3(2H)-one derivatives were synthesized by one-pot multicomponent cyclocondensation of ketoacid, thiosemicarbazide, and phenacyl bromide using catalytical amount of KSF in EtOH under reflux. The straightforward synthesis, presence of two important class of heterocyclic rings in the individual molecule, easy workup of the products, rapid reaction, mild conditions, and good to excellent yields are notable features of this protocol.

[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]     

Borax: An Ecofriendly and Efficient Catalyst for One-Pot Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones under Solvent-Free Conditions

Borax in the presence of a very small amount of 5 M sulfuric acid efficiently catalyses the three-component condensation of an aldehyde, β-ketoester, and urea or thiourea to afford the corresponding 3,4-dihydropyrimidin-2(1H)-ones or 3,4-dihydropyrimidin-2(1H)-thiones in good to excellent yields under solvent-free conditions at 80 °C. Compared with the classical Biginelli reaction conditions, this new method has the advantage of excellent yield, short reaction time (1–2 h), easy workup, and no use of volatile organic solvent.     

Alternate Synthesis Route of 2-(Substituted Phenyl)-3,3a-dihydro-8H-pyrazolo[5,1-a]isoindol-8-ones via Chalcone-Based N-Formyl-pyrazolines

An alternate approach to 2-(substituted phenyl)-3,3a-dihydro-8H-pyrazolo[5,l-a] isoindol-8-ones via chalcone-based N-formyl-pyrazolines is described. N-Formyl-pyrazolines were prepared in excellent yield (81–96%) by the reaction of chalcones with hydrazine hydrate in the presence of formic acid, which undergoes intramolecular Friedel–Crafts acylation in the presence of trifluoroacetic acid (TFA) as a catalyst to afford functionalized 2-(substituted phenyl)-3,3a-dihydro-8H-pyrazolo[5,1-a]isoindol-8-ones in good to excellent yield (74–94%) at reflux in acetonitrile. Our synthetic route avoids expensive reagents and significantly improves yields.     

Simple and Efficient Synthesis of 2-Aryl-2,3-Dihydroquinolin-4(1H)-ones Using Silica Chloride as a New Catalyst Under Solvent-Free Conditions

A mild, efficient, and high-yielding method for the synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones from their corresponding 2-amino chalcones using silica chloride (SiO₂Cl) under solvent-free conditions is described. A series of 2-aryl-2,3-dihydroquinolin-4(1H)-ones containing both electron-donating and electron-withdrawing substituents were synthesized.     

Synthesis and structure of 1,3-dialkyl-4-(sulfonylimino)imidazolidin-2-ones

The reactions of 1,3-dialkyl-4,5-dihydroxyimidazolidin-2-ones with alkyl sulfamides have been studied and previously undescribed 1,3-dialkyl-4-(alkylaminosulfonylimino)imidazolidin-2-ones have been obtained. The structure of 1,3-dimethyl-4-(benzenesulfonylimino)imidazolidin-2-one was investigated by X-ray structural analysis. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1159–1166, August, 2007.     

Convenient Synthesis of 5-Alkylfuran-2(5H)-ones

A convenient synthesis of 5-alkylfuran-2(5H)-ones are described starting from 3-nitropropanoate and aldehydes, promoted by neutral alumina, in 35–60% overall yields, via a condensation–lactonization–elimination pathway.      

基于龙胆苦苷的二吲哚甲烷类拟单萜吲哚生物碱类似物合成及其抗肿瘤、逆转紫杉醇耐药活性研究

以环烯醚萜类化合物龙胆苦苷为合成模块,利用拟单萜吲哚生物碱的仿生合成途径和组合化学的研究思路,与色胺类衍生物(吲哚结构的活性单元片段)通过缩合反应,首次合成了23个二吲哚甲烷类拟单萜吲哚生物碱类似物。利用核磁共振波谱(NMR)和高分辨质谱(HRMS)等谱学手段对合成化合物的结构进行了表征,并初步评价了其抗肿瘤活性和逆转耐药活性。活性结果表明,化合物4i脱掉糖基保护基后的化合物5i对3种肿瘤细胞系(TE-1,CAL-62和FaDu)的抑制作用强于阳性对照盐酸阿霉素(Dox)。通过与紫杉醇的联合用药,发现部分化合物如4m、4n、4o、4r等能够有效降低人肺癌细胞紫杉醇耐药株A549/Taxol对紫杉醇的耐药性,具有良好的逆转耐药潜力。     

Synthesis of Some Heterocyclic Compounds from Enamines of 3-Acetylfuran-2(5 H)-ones

The interaction of different 3-acetylfuran-2(5H)-ones (1, 4) with dimethylformamide dimethyl acetal (DMF/DMA) has been investigated, and the condensed furopyridine system 3 was obtained. By means of interaction of compounds 4 and DMF/DMA via the 3-acetylfuran-2(5H)-one enamines, the heterocyclic substituted furanones are obtained. The condensation of 3-acetyl-4,5,5-trimethylfuran-2(5H)-one (1a) with veratraldehyde was realized. Through the interaction of 1a with malononitrile and further intramolecular condensation of the product, 6-amino-dihydroisobenzofuran-5-carbonitrile was also synthesized.     

1,8-二(2-吡咯酰胺)-3,6-二氯咔唑的合成、晶体结构及阴离子识别研究

设计并合成了1,8-二(2-吡咯酰胺)-3,6-二氯咔唑化合物(1), 利用X射线单晶衍射研究了该化合物的固态结构. 利用荧光和紫外-可见光谱技术及¹H NMR滴定法研究了其对阴离子的识别. 研究结果表明, 化合物1对H₂PO₄^-离子有较强的识别能力, 且对H₂PO₄^-离子有明显的荧光增强效应, 可用来识别H₂PO₄^-离子. 同时¹H NMR滴定结果显示, 化合物1在阴离子识别过程中发生了构型转化.