Ultrasound-promoted one-pot, three-component synthesis of spiro[indoline-3,1'-pyrazolo[1,2-b]phthalazine] derivatives

A series of 3'-aminospiro[indoline-3,1'-pyrazolo[1,2-b]phthalazine]-2,5',10'-trione derivatives have been synthesized by a one-pot three-component reaction of isatin, malononitrile or ethyl cyanoacetate and phthalhydrazide catalyzed by piperidine under ultrasound irradiation. For comparison the reactions were carried out under both conventional and ultrasonic conditions. In general, improvement in rates and yields were observed when the reactions were carried out under sonication compared with classical conditions.     

Simple synthesis of 7H-phenaleno[1,2-b]furan-7-one derivatives by one-pot, three-component reactions

The reaction of alkyl isocyanides with various aldehydes and 3-hydroxy-1 H-phenalene-1-one is described. The protocol offers facile and efficient synthesis of biologically interesting 9-(alkyl or arylamino)-7 H-phenaleno[1,2- b]furan-7-one derivatives from readily available starting materials in high yields.     

室温下Cu掺杂的ZnO纳米粉末催化多组分一锅法合成完全取代的茚并[1,2-b]吡啶(英文)

Cu doped ZnO nanocrystalline powder(10 mol%) has been found to be an efficient catalyst for the one‐pot multi‐component synthesis of fully substituted new indeno[1,2‐b]pyridines through a com-bination of 1,3‐indandione, propiophenone or acetophenone derivatives, aromatic aldehydes, and ammonium acetate in ethanol/H2 O at room temperature. The methodology is mild, efficient and high to excellent yielding.     

One-pot synthesis of acenaphtho[1,2-b]furan derivatives

New 9-(alkyl or aryl)acenaphtho[l,2-b]furan-8-(alky or aryl)amine compounds has herein been reported by one-pot reaction of (acenaphthylen-l-yloxy)trimethylsilane,alkyl and aryl aldehydes,and aryl and alky isocyanides in refluxing DMF.     

Ultrasound promoted three-component synthesis of dihydroindeno[1,2-b]pyrrole derivatives

In this work, a one-pot three-component reaction of ninhydrin, primary amines, and 1,3-dicarbonyl compounds was investigated under various conditions to synthesis of diverse derivatives of dihydroindeno[1,2-b]pyrroles. Catalyst-free conditions in EtOH under ultrasound irradiation (45% of amplitude) were selected as a novel and efficient method for synthesis of these fused structures. The reactivity of different primary amines was then investigated for steric and electronic effects. Two examples of difunctional structures were also synthesized by using of 1,4-diaminobenzene under optimum conditions with high yields. The structure of all products was characterized by spectroscopic methods and elemental analysis.     

Grindstone chemistry: one-pot synthesis of spiro[diindenopyridine-indoline]triones and spiro[acenaphthylene-diindenopyridine]triones

A one-pot, pseudo four-component, and simple synthesis of spiro[diindenopyridine-indoline]triones and spiro[acenaphthylene-diindenopyridine]triones via the reaction of 1,3-indandione, aromatic amines and isatins or acenaphthylene-1,2-dione using a ‘Grindstone Chemistry’ method is reported.     

Facile synthesis of 1H-pyrazolo[1,2-a]pyridazine-5,8-dione derivatives by a one-pot, three-component reactions

Protonation of the highly reactive 1:1 intermediate produced in the reaction between alkyl or aryl isocyanides and electron-deficient acetylenic esters with 3,6-dihydroxypyridazine, leads to a vinylisonitrilium cation, which undergoes an addition reaction with the conjugate base of the 3,6-dihydroxypyridazine to produce dialkyl 3-(alkyl or arylamino)-5,8-dioxo-5,8-dihydro-1H-pyrazolo[1,2-a]pyridazine-1,2-dicarboxylates in good yields at room temperature.     

无过渡金属参与下茚并-[1,2-b]吲哚-10(5H)-酮的合成

发展了一种从3-(2-溴代苯甲酰基)-吲哚出发在无过渡金属参与下合成茚并吲哚酮类化合物的新方法。在甲苯/四氢呋喃(2∶1)混合溶剂中,3-(2-溴代苯甲酰基)-吲哚、正丁基锂和碘化锌原位生成的2-吲哚锌在碘化锂辅助下与芳基溴化物发生分子内加成-环化反应,合成了一系列取代的茚并-[1,2-b]吲哚-10(5H)-酮类化合物,且均获得了较好的收率。考察了溶剂、卤化锌、添加剂对产率的影响。     

A one-pot three-component approach to synthesis of novel dihydroxyoxoindeno[1,2-b]pyrrole derivatives

A new class of 2-arylamino-dihydroxyindenopyrroles were prepared by the one-pot multicomponent reaction of ninhydrin, N-methyl-1-(methylthio)-2-nitroethenamine and aromatic amines in EtOH at room temperature. The advantages of this procedure are short reaction times, good to high yields, easy separation of products and good functional group tolerance.     

An efficient one-pot three-component synthesis of functionalized pyrimido[4,5-b]quinolines and indeno fused pyrido[2,3-d]pyrimidines in water

A simple, efficient, and high yielding one-pot protocol for the synthesis of pyrimido[4,5-b]quinolines and indeno[2′,1′:5,6]pyrido[2,3-d]pyrimidines has been developed by three-component domino coupling of 6-amino-1,3-dimethyluracil, aldehydes, and cyclic 1,3-diketones in ecofriendly solvent water promoted by PTSA. The protocol avoids the use of expensive catalysts, toxic solvents, and chromatographic separation. The generality and functional tolerance of this convergent and environmentally benign method is demonstrated.     

p-Toluenesulfonic acid-catalyzed one-pot synthesis of 2-amino-4-substituted-1,4-dihydrobenzo[4,5]imidazolo[1,2-a]pyrimidine-3-carbonitriles under neat conditions

A simple, efficient, and green procedure for the preparation of 2-amino-4-substituted-1,4-dihydrobenzolo[4,5]imidazolo[1,2-a]pyrimidine-3-carbonitriles has been developed by multi-component condensation of 2-aminobenzimidazole with aldehydes and malononitrile in the presence of a catalytic amount of p-toluenesulfonic acid, affording excellent yields under neat conditions. The protocol avoids the use of expensive catalysts, toxic solvents, and chromatographic separation. We believe that this new environmentally metal-free procedure, combined to a solvent-free reaction, would be of importance in the search of green laboratory-scale synthesis.     

An efficient and novel protocol for the synthesis of spiro[1,3]oxazino[5,6-c]quinoline derivatives by one-pot,three-component reaction

Research on Chemical Intermediates - One-pot, three-component reaction of various aryl glyoxal monohydrates, 5-methylisoxazol-3-amine and 4-hydroxyquinolin-2(1H)-one in the presence of a catalytic...     

Synthesis of highly functionalized indeno[1,2-b]furans

Some novel functionalized indeno[1,2-b]furans were synthesized from the reaction of indandione/indanone and aldehydes at room temperature followed by the reaction of the Knoevenagel condendensed intermediate with 4-hydroxycoumarins in the presence of iodine as catalyst in dimethyl sulfoxide (DMSO) under thermal conditions. The reaction involved in a condensation and Michael addition followed by lactone ring opening and intramolecular cyclization process to afford the product in high yield in easy work-up procedure.     

Efficient polymeric catalyst for one-pot synthesis of acenaphtho[1,2-b]pyrroles

Some new derivatives of acenaphtho[1,2-b]furans have been synthesized efficiently by one-pot reaction of (acenaphthylen-1-yloxy)trimethylsilane, various aldehydes, and isocyanides in the presence of silica-supported ionic liquid.     

A DMAP-catalyzed mild and efficient synthesis of 1,2-dihydroquinazolines via a one-pot three-component protocol

An efficient and simple method for the synthesis of 1,2-dihydroquinazolines catalyzed by 4-(N,N-dimethylamino)pyridine (DMAP) from readily available aromatic or heteroaromatic aldehydes, 2-aminobenzophenone, and ammonium acetate under mild conditions is described. The scope and limitations of the method are discussed.     

InBr3-catalyzed three-component, one-pot synthesis of imidazo[1,2-a]pyridines

Indium(III) bromide has been used for the first time for the synthesis of imidazo[1,2-a]pyridines in a one-pot operation from 2-aminopyridine, aldehydes, and alkynes. InBr₃ was found to be more effective for the activation of both alkyne and imine derived from aryl aldehyde and 2-aminopyridine.     

6H-吲哚[2,3-b]并喹喔啉衍生物的合成及荧光性能研究

报道了以7-甲(乙)基靛红(1a,1b)为原料,对其1-烃基化得1-烃基-7-甲(乙)基靛红(2a1-2a5,2b1-2b5)。1a,1b,2a1-2a5,2b1-2b5与邻苯二胺在冰醋酸为溶剂或以水为溶剂,四丁基溴化铵(TBAB)为相转移催化剂,采用改进的工艺进行缩合反应,以70.0%-85.8%的收率合成了一系列结构新颖的含有1,4-二氮杂萘结构的吲哚类化合物3a-3b,3a1-3a5,3b1-3b5。化合物3a1-3a5,3b1-3b5为新化合物,其结构经红外光谱、质谱、核磁氢谱(碳谱)确认。荧光光谱测定表明,化合物3a-3b,3a1-3a5,3b1-3b5具有很好的荧光性能。     

Efficient and direct synthesis of poly-substituted indeno[1,2-b]quinolines assisted by p-toluene sulfonic acid using high-temperature water and microwave heating via one-pot, three-component reaction

Reactions of aldehydes, 1,3-indanedione and enaminones were successfully carried out using p-toluene sulfonic acid (p-TsOH) as a catalyst and high-temperature water as a solvent under microwave irradiation. This method provided several advantages such as rapid reaction times, high yields, and a simple workup procedure. In addition, a possible mechanism to account for the reaction was proposed.     

Synthesis of cyclopropa[c]indeno[1,2-b]quinolines through a MCR/Staudinger/aza-Wittig sequence

Spirocyclopropanes were prepared from aromatic aldehydes, 1,3-indandione and acetophenones through a halogenation/S_N2-displacement/Michael-initiated ring-closing sequence by a pyridinium-ylide-assisted multicomponent reaction, and their further use was also researched in the construction of cyclopropa[c]indeno[1,2-b]quinolines through subsequent Staudinger/aza-Wittig reactions.