One pot,three component synthesis of spiroindenoquinoxaline pyrrolidine fused nitrochromene derivatives following 1,3-dipolar cycloaddition

An expedient one-pot sequential three-component synthesis of a series of diverse spiroindenoquinoxaline pyrrolidine fused nitrochromene derivatives following 1,3-dipolar cycloaddition of azomethine ylides generated in situ by the condensation of indenoquinoxalone and α-amino acids (L-proline and L-phenyl alanine) with 3-nitrochromenes as dipolarophile under classical as well as microwave irradiation is described. The protocol provides a mild reaction condition, high yield of the products, high regioselectivity, and operational simplicity to assemble complex structural entity in a single operation with good to excellent yield. The regio and stereochemical outcome of the cycloaddition reaction is ascertained by spectroscopic and single crystal X-ray analysis.     

Synthesis of dispirooxindolecycloalka[d]pyrimidino[2,3-b]-thiazole pyrrolidine/thiapyrrolizidine ring systems

The synthesis of a new class of spirooxindolo pyrrolidines and spirooxindolo thiapyrrolizidines has been accomplished by a three component, one-pot 1,3-dipolar cycloaddition reaction. The cycloaddition was found to be highly regioselective.     

1,3-Dipolar cycloaddition reaction for diastereoselective synthesis of functionalized dihydrospiro[indoline-3,2'-pyrroles]

The BF₃OEt₂ catalyzed one-pot 1,3-dipolar cycloaddition reaction of benzylamines, isatins and dimethyl acetylenedicarboxylate in dry methylene dichloride afforded the functionalized dihydrospiro[indoline-3,2'-pyrroles] in moderate to good yields and with high diastereoselectivity. The reaction was accomplished by the tandem 1,3-dioplar cycloaddition of in situ generated azomethine ylide with acetylenedicarboxylate and the nucleophilic addition of pyrrole ring to second molecular acetylenedicarboxylate.     

An easy access to novel steroidal dispiropyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides

A facile one-pot synthesis of novel steroidal dispiropyrrolidines has been accomplished by 1,3-dipolar cycloaddition reaction of various azomethine ylides derived from isatin/acenaphthenequinone/ninhydrin and sarcosine with various estrone derivatives as dipolarophiles, in good yield. The effect of various solvents on the 1,3-dipolar cycloaddition reaction are also studied.     

An expedient diastereoselective synthesis of pyrrolidinyl spirooxindoles fused to sugar lactone via [3+2] cycloaddition of azomethine ylides

Synthesis of pyrrolidinyl-spirooxindoles fused to sugar lactone has been achieved by a one pot three component 1,3-dipolar cycloaddition (1,3-DC) reaction. A unique dipolarophile (α,β-unsaturated lactone) derived from d-glucose/d-galactose reacted with azomethine ylide generated in situ from isatin/N-substituted isatin and secondary amino acids (sarcosine/proline/piperidine-2-carboxylic acid) to give the corresponding cycloadducts in good yield. The cycloaddition was found to be highly regio- and diastereoselective.     

Synthesis of novel spiro-[3H-indole-3,3′-[1,2,4]triazolidine]-2-ones via azomethine imines

Novel spiroindoles 5 are prepared easily via a one-pot, 1,3-dipolar cycloaddition reaction of azomethine imines with isatin imines under thermal conditions.     

An expedient synthesis of pyrrolidinyl spirooxindole grafted 3-nitrochromanes through 1,3-dipolar cycloaddition reaction of azomethine ylides

A facile one-pot synthesis of pyrrolidinyl-spirooxindole grafted 3-nitrochromanes has been accomplished by 1,3-dipolar cycloaddition (1,3-DC) reaction of 3-nitrochromenes with azomethine ylides generated in situ from isatin and secondary amino acids. The regio- and stereochemical outcome of the cycloaddition reaction was ascertained by X-ray crystallographic analysis.     

One-pot,five-component 1,3-dipolar cycloaddition: A facile synthesis of spiropyrrolidine and spiropyrrolizidine derivatives

A one-pot, five-component strategy toward the synthesis of new indole substituted pyrrolidine and pyrrolizidine heterocycles through 1,3-dipolar cycloaddition reactions using ninhydrin, 1,2-phenylenediamine, amino acids, 3-cyanoacetyl indoles and aryl aldehydes is described. The features of this procedure were characterized by the mild reaction conditions, high yields, one-pot procedure, and operational simplicity.     

Facile One-Pot Synthesis of Ferrocene-Based Spiropyrrolidines and Pyrrolizidines Through 1,3-Dipolar Cycloaddition Reaction

A facile and efficient synthesis of ferrocene-based spiroacenaphthenone pyrrolidines and pyrrolizidines through a one-pot, three component 1,3-dipolar cycloaddition reaction is described.     

1,3-Dipolar cycloaddition of organic azides to alkynes by a dicopper-substituted silicotungstate

The dicopper-substituted gamma-Keggin silicotungstate TBA 4[gamma-H2SiW10O36Cu2(mu-1,1-N3)2] (I, TBA = tetra- n-butylammonium) could act as an efficient precatalyst for the regioselective 1,3-dipolar cycloaddition of organic azides to alkynes. Various combinations of substrates (four azides and eight alkynes) were efficiently converted to the corresponding 1,2,3-triazole derivatives in excellent yields without any additives. The present system was applicable to a larger-scale cycloaddition of benzyl azide to phenylacetylene under solvent-free conditions (100 mmol scale) in which 21.5 g of the analytically pure corresponding triazole could be isolated. In this case, the turnover frequency and the turnover number reached up to 14,800 h(-1) and 91,500, respectively, and these values were the highest among those reported for the copper-mediated systems so far. In addition, I could be applied to the one-pot synthesis of 1-benzyl-4-phenyl-1H-1,2,3-triazole from benzyl chloride, sodium azide, and phenylacetylene. The catalyst effect, kinetic, mechanistic, and computational studies show that the reduced dicopper core plays an important role in the present 1,3-dipolar cycloaddition.     

1,3-偶极环加成反应与控制自由基聚合结合制备嵌段共聚物的研究进展

炔基与叠氮基的1,3-偶极环加成反应作为点击化学的精髓,反应高效,条件温和.通过它与控制自由基聚合结合,为制备多种拓扑结构嵌段共聚物提供了新途径,所得嵌段共聚物纯度高,分子量分布较窄.本文就1,3-偶极环加成点击反应与3种控制自由基聚合方法相结合在制备线型及非线型嵌段共聚物方面所取得的成就加以综述,并对今后的发展方向做...     

Chiral phosphoric acid catalyzed 1,3-dipolar cycloadditions of aldehydes,diethyl α-aminomalonate,and nitroalkenes

A one-pot three component 1,3-dipolar cycloaddition reaction of an aldehyde, α-aminomalonate, and nitroalkene has been developed through binaphthol derived chiral phosphoric acids. This reaction represents one of the most enantioselective catalytic approaches to access structurally diverse pyrrolidine derivatives.     

Synthesis of novel 1,4-disubstituted 1,2,3-triazoles bearing organosilicon-sulfur groups via the click reaction sonocatalyzed by LaCuxMn1-xO3 nanoparticles

A highly efficient and environmentally friendly one-pot procedure for the synthesis of 1,2,3-triazoles by 1,3-dipolar cycloaddition of benzyl halides, terminal alkynes, and sodium azide over LaCu_xMn_1-xO₃ perovskite oxides was developed. LaCu_0.7Mn_0.3O₃ was found to be active with low catalyst loading under ultrasonic irradiation in aqueous media. The reaction was performed efficiently in the presence of the nanocatalyst in the absence of any additive or base with a noticeable reduction in the reaction time. The catalyst could be recycled and reused at least five times without any significant effect on the results of the reaction. Moreover, a series of novel organosilicon-sulfur substituted 1,2,3-triazole derivatives was synthesized using carbon disulfide and tris(trimethylsilyl)methylithium.     

Enantioselective synthesis of the spirotryprostatin A scaffold

The pentacyclic spirotryprostatin scaffold embodies an oxindole with an all-carbon quaternary stereocenter. The scaffold can efficiently be accessed in a one-pot reaction sequence consisting of a highly enantioselective 1,3-dipolar cycloaddition, N-acylation of the resulting stereochemically complex 3,3′-pyrrolidinyl-spirooxindole core with Fmoc-proline and spontaneous ring closure upon N-deprotection.     

Stereoselective synthesis of oxazolidine, hexahydropyrrolo [2,1-b] oxazole, and tetrahydro-2H-oxazolo [3,2-c] thiazole grafted macrocycles through intramolecular 1,3-dipolar cycloaddition reaction

A facile one-pot synthesis of oxazolidine, hexahydropyrrolooxazole and tetrahydro-2H-oxazolothiazole grafted macrocycles through intramolecular 1,3-dipolar cycloaddition reaction (1,3-DC reaction) is reported. X-ray diffraction studies and 2D NOESY experiments of the cycloadducts proved the stereo- and regiochemistry of the cycloaddition.     

Solid-phase synthesis of 1,2-diheterocyclic-substituted (E)-olefins from a supported selenium resin

A library of 1,2,3-triazoles, isoxazoles, 1,2,4-oxadiazoles, and isoxazoline-containing 1,2-di-heterocyclic-substituted compounds with three points of diversity linked by an E double bond were prepared. Key steps include a 1,3-dipolar cycloaddition and Porco's two-step, one-pot condensation and alpha-alkylation reaction of selenium resins.     

A novel one-pot method for the preparation of pyrazoles by 1,3-dipolar cycloadditions of diazo compounds generated in situ

A convenient one-pot procedure for the preparation of pyrazoles by 1,3-dipolar cycloaddition of diazo compounds generated in situ has been developed. Diazo compounds derived from aldehydes were reacted with terminal alkynes to furnish regioselectively 3,5-disubstituted pyrazoles. Furthermore, the reaction of N-vinylimidazole and diazo compounds derived from aldehydes gave exclusively 3-substituted pyrazoles in a one-pot process.     

A facile regio- and stereoselective synthesis of novel spiro[indolin-3,2′-pyrrolidin]-2-one’s via 1,3-dipolar cycloaddition of azomethine ylides

A facile regio and stereoselective synthesis of novel spiro[indolin-3,2′-pyrrolidin]-2-one’s have been accomplished through 1,3-dipolar cycloaddition of azomethine ylides generated in situ from the reaction of isatin and benzyl amine with quinoline bearing dipolarophiles in good yields. The synthesized compounds were well characterized through different spectroscopic techniques, such as single crystal XRD, FTIR, NMR, and mass spectral analysis.     

A facile one-pot three-component synthesis of ferrocene-grafted dispiro pyrrolidine/pyrrolizidine scaffolds through intermolecular [3+2] cycloaddition reaction of ferrocenyl Baylis-Hillman adduct

A one-pot synthesis of ferrocene-grafted dispiropyrrolidine/pyrrolizidine scaffolds has been accomplished in good yields through a facile 1,3-dipolar cycloaddition of various azomethine ylides derived from diketones and secondary amino acids with Baylis-Hillman adduct derived from ferrocene carbaldehyde. The regiochemical and stereochemical outcomes of the cycloaddition reaction were ascertained by X-ray crystallographic studies of one of the cycloadducts.     

TiO2-Mediated,One-Pot,Four-Component 1,3-Dipolar Cycloaddition Reaction: A Facile Synthesis of Dispiro-pyrrolidine Ring Systems

An expedient regioselective synthesis of dispiroindenoquinoxaline pyrrolidine derivatives mediated by TiO₂ in a one-pot, four-component 1,3-dipolar cycloaddition reaction is described.