One-pot synthesis of functionalized hydantoin derivatives via a four-component reaction between an amine, an arylsulfonyl isocyanate and an alkyl propiolate or dialkyl acetylenedicarboxylate in the presence of triphenylphosphine

An effective route to functionalized hydantoin derivatives is described, involving the reaction of a urea derivative resulting from the addition of a primary amine to an arylsulfonyl isocyanate, and an alkyl propiolate or dialkyl acetylenedicarboxylate in the presence of triphenylphosphine. The reactive 1:1 intermediate obtained from the addition of triphenylphosphine to the alkyl propiolate or dialkyl acetylenedicarboxylate was trapped by NH-acids such as the urea derivative to produce functionalized hydantoin derivatives.     

Two intermediates in the reaction between dibenzoylacetylene and enol systems in the presence of triphenylphosphine in THF/H2O

Abstract  The reaction between dibenzoylacetylene and enol systems, such as acetylaceton or cyclohexane-1,3-dione in the presence of triphenylphosphine in THF/H₂O, leads to 4-acetyl-3-benzoyl-1-phenyl-1,5-hexanedione and 2-hydroxy-3-(2-oxo-2-phenylethyl)-2-phenyl-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one. Subsequently, these compounds undergo cyclization and elemination reactions in acidic dichloromethane at room temperature to produce known highly functionalized furan derivatives. Graphical abstract        

One-pot three-component synthesis of the spiroacenaphthylene derivatives

A facile and efficient one-pot three-component synthesis of the spiroacenaphthylene derivatives was achieved, via the reaction of acenaphthequinone, malononitrile/ethylcyanoacetate and various reagents including α-methylencarbonyl compounds/enols.     

Synthesis of functionalized iminolactones via an isocyanide-based three-component reaction

A three-component reaction of the zwitterions generated from isocyanides and dialkyl acetylenedicarboxylate with 1-(4-bromophenyl)-2-thiocyanatoethanone or 1-phenyl-2-thiocyanatoethanone is described. The reaction afforded the corresponding special type of functionalized iminolactone derivatives in good yields at room temperature without using a catalyst.     

One-pot synthesis of 4,5-dihydro-1H-pyrrol-3-carboxamide derivatives via a four-component reaction

An effective route to functionalized 4,5-dihydro-1H-pyrrol-3-carboxamide derivatives is described. This involves reaction of N-alkyl-3-oxobutanamides, which result from the addition of an amine to the diketene, and a primary amine in the presence of dibenzoylacetylene. The 1,3-dicarbonyl compounds obtained from the addition of an amine to diketene were trapped with a primary amine to produce (Z)-3-(alkylamino)-N¹-alkyl-2-butenamide, which reacts with dibenzoylacetylene to produce 4,5-dihydro-1H-pyrrol-3-carboxamide derivatives.     

Regio and diastereoselective synthesis of functionalized 2,3-dihydrofuro[3,2-c]coumarins via a one-pot three-component reaction

An efficient and straightforward synthesis of furo[3,2-c]coumarins via the one-pot three-component condensation of aromatic aldehydes, 4-hydroxycoumarin and α-chloroketones in refluxing n-propanol is described. Pyridine or a mixture of AcOH and AcONH₄ was used as a basic catalyst.     

One-pot synthesis of tetrahydrofuran derivatives via a divalent palladium-catalyzed three-component coupling

Under divalent palladium catalysis, a three-component coupling reaction for synthesizing tetrahydrofuran derivatives has been established. The reaction involves the intramolecular carbopalladation of an alkyne with a carbanion which was generated from the addition of an alkoxide ion to an alkene derivative, followed by allylic chloride insertion to the CPd bond and quenching the CPd bond by β-heteroatom elimination in the presence of excess chloride ions.     

Divergent synthesis of functionalized thioethers via multicomponent reaction of benzynes

Diverse functionalized thioethers were efficiently synthesized through the multicomponent reaction of benzynes, cyclic thioethers and different nucleophiles. Both inorganic salts (KF, KCl, KBr, and KSCN) and silylated reagents (TMSCN, TMSN₃, TMSCl) can be utilized as efficient nucleophiles for the reaction.     

One-pot synthesis of functionalized thioureas by reaction of benzoyl isothiocyanates, secondary amines, and alkyl propiolates

An efficient one-pot synthesis of functionalized thioureas is described via three-component reaction of benzoyl isothiocyanates, secondary amines, and alkyl propiolates in the presence of triphenylphosphine (20 mol%). Correspondence: Issa Yavari, Chemistry Department, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran     

Stereoselective synthesis of 2-hydroxymorpholines and aminodiols via a three-component boro-Mannich reaction

The three-component coupling of an 1,2-aminoalcohol, a 1,2-dicarbonyl compound and a boronic acid was investigated. The reaction is supposed to proceed through the formation of a heterocyclic iminium species followed by the addition of the organoboron derivative. The diastereoselectivity of this process is discussed. Best results were observed when the probable intermediate was generated from a preformed 3-phenylthiomorpholin-2-ol. Products of this three-component boro-Mannich could be readily converted to the corresponding aminodiols by reduction with lithium aluminium hydride.     

An atom-economic synthesis of functionalized pyrroles via a sequential metal-catalyzed three-component reaction

A three-component reaction of one molecule of imine and two molecules of alkynoates is realized with the catalysis of Cu(I)–Fe(III) in a sequential manner to allow the direct synthesis of functionalized pyrroles, during which, one C–N bond and two C–C bonds are formed with high atom economy. This method benefits from easily available starting materials, low-cost catalysts, and convenient operations.     

Three-component reaction of triphenylphosphine,dialkyl but-2-ynedioate and arylidene pivaloylacetonitrile for diastereoselective synthesis of densely substituted 2,3-dihydrofurans

The three-component reaction of triphenylphosphine,dialkyl but-2-ynedioate and arylidene pivaloylacetonitrile in dry methylene dichloride at room temperature resulted in unexpected densely substituted 1-(triphenyl-λ~5-phosphanylidene)ethyl)-2,3-dihydrofurans in satisfactory yields with high diastereoselectivity.The relative configuration of the 2,3-dihydrofurans was elucidated by determination of single crystal structures.     

An efficient one-step synthesis of 1,4-dihydropyridines via a triphenylphosphine-catalyzed three-component Hantzsch reaction under mild conditions

An efficient one-step synthesis of 1,4-dihydropyridines in good to excellent yields via the triphenylphosphine-catalyzed Hantzsch three-component reaction of an aromatic aldehyde, ethyl acetoacetate and ammonium acetate is described.     

Reaction between triphenylphosphine and aromatic amines in the presence of diethyl azodicarboxylate: an efficient synthesis of aryliminophosphoranes under neutral and mild conditions

An efficient synthesis of aryliminophosphoranes is described. A mixture of an aromatic amine, diethyl azodicarboxylate and triphenylphosphine undergo a Mitsonobu type reaction at ambient temperature in dry dichloromethane to afford aryliminophosphoranes in excellent yields.     

Molecular iodine-catalyzed and air-mediated tandem synthesis of quinolines via three-component reaction of amines, aldehydes, and alkynes

A one-pot synthesis of quinolines via molecular iodine-catalyzed and air-mediated tandem condensation/imino-Diels-Alder/isomerization/oxidation of simple readily available amines, aldehydes, and alkynes has been developed. This methodology was extended to synthesize quinazolines from two molecules of amines and two molecules of glyoxalates.     

An efficient synthesis of benzodiazepine derivatives via a one-pot,three-component reaction accelerated by a chitosan-supported superparamagnetic iron oxide nanocomposite

This work describes the catalytic ability of Fe₃O₄@chitosan as an environmentally benign and stable composite nanocatalyst for the synthesis of benzodiazepine derivatives starting from o-phenylenediamine, dimedone, and different aldehydes via a one-pot, three-component reaction at room temperature. High-to-excellent yields, easy work-up, reusability of the nanocatalyst, and non-toxicity are some of the advantages of this protocol.     

One-pot three-component synthesis of functionalized spirolactones by means of reaction between aromatic ketones, dimethyl acetylenedicarboxylate, and N-heterocycles

A simple and convenient one-pot multi-component reaction has been described for the synthesis of functionalized spirolactones. This strategy demonstrated three-component reaction between aromatic ketones (11H-indeno[1,2-b]quinoxalin-11-one) and dimethyl acetylenedicarboxylate (DMAD) in the presence of N-heterocycles, such as pyridine, quinoline, and isoquinoline in CH₂Cl₂ at ambient temperature without use of any catalyst or activator.     

One-pot,three-component synthesis of highly functionalized pyrimidone derivatives and access to indole fused pyrimidones via palladium-catalyzed intramolecular Heck reaction

A simple and facile approach to highly functionalized pyrimidone derivatives and indole fused pyrimidones has been developed. The synthesis of substituted pyrimidone derivatives in moderate to good yields involves [4+2] cycloaddition of 1,4-dipoles generated from α,β-unsarurated imines and dimethyl acetylenedicarboxylate (DMAD) with isocyanates as dipolarophiles. Furthermore, the pyrimidones resulted from 2-bromophenyl isocyanate could be transformed into various indole fused pyrimidones via intramolecular palladium-catalyzed Heck reaction under different conditions.     

Trifluoroacetylation of amines with trifluoroacetic acid in the presence of trichloroacetonitrile and triphenylphosphine

We developed a mild and convenient trifluoroacetylation process for amines using a combination of trichloroacetonitrile and triphenylphosphine. The reaction that we designed is applicable to the trifluoroacetylation of a wide variety of amines, including amines with stereogenic centers, which underwent trifluoroacetylation without racemization.     

Catalyst-free synthesis of 3-(1-arylsulfonylalkyl)indoles via three-component reaction of indoles,carbonyls, and arenesulfinic acids

A catalyst-free three-component reaction of indoles, carbonyls, and arenesulfinic acids performed at room temperature provides direct access to biologically important 3-(1-arylsulfonylalkyl)indoles. This process features mild conditions, low cost, broad substrate scope, and high yields, and mechanistically bis(indolyl)methanes were identified as the key intermediates.