Novel multicomponent reaction for the combinatorial synthesis of 2-imidazolines

[reaction: see text] The three-component condensation between an amine, an aldehyde, and an alpha-acidic isocyanide efficiently provides substituted 2-imidazolines in a one-pot reaction under mild conditions.     

An isocyanide based multi-component reaction under catalyst- and solvent-free conditions for the synthesis of unsymmetrical thioureas

A new and efficient method for the synthesis of thiourea derivatives by a sequential one-pot, three-component reaction between aromatic isocyanides, amines, and 1,2-di-tert-butyldisulfane (DTBS) was developed and 27 different examples were synthesized in good to excellent yields. DTBS was identified as an effective sulfur surrogate without the use of both catalysts and solvents. This protocol does not employ any transition metal catalyst or special experimental setup.     

A novel three-component reaction of allenoates, isocyanides, and carboxylic acids: facile synthesis of highly substituted acryl imide derivatives

A novel synthesis of highly substituted acryl imide derivatives by the three-component reaction of allenoates, isocyanides, and carboxylic acids was reported, and the intramolecular cyclization reaction of allenoic acids with isocyanides was also described.     

Silver-Catalyzed Three-Component 1,1-Aminoacylation of Homopropargylamines: α-Additions for Both Terminal Alkynes and Isocyanides

The reaction of secondary homopropargylamines, isocyanides, and water in the presence of a catalytic amount of silver acetate and subsequent purification by chromatography on silica gel afforded substituted proline amides in good to excellent yields. Primary homopropargylamines underwent a cyclizative Ugi–Joullié three-component reaction with isocyanides and carboxylic acids to afford functionalized N-acyl proline amides. High diastereoselectivity was observed in the synthesis of 4-alkoxy and 4,5-disubstituted proline derivatives. This work represents the first examples of a three-component cyclizative 1,1-aminoacylation of terminal alkynes.     

Tandem oxidative isocyanide-based cycloaddition reactions in the presence of MIL-101(Cr) as a reusable solid catalyst

The tandem oxidative three-component synthesis of two types of the heterocycles such as furans and imidazopyridines, via isocyanides [1+4] cycloaddition reactions in the presence of MIL-101(Cr) under aerobic conditions are reported. When the 4-toluenesulfonylmethyl isocyanide was used, an unexpected [3+2] cycloaddition reaction of isocyanides with aldehydes accomplished and dihydrophenyloxazoles and phenyloxazoles produced. These syntheses were successfully carried out using a wide scope of the substrates.     

Isocyanide-based multicomponent reactions: synthesis of alkyl-2-(1-(alkylcarbamoyl)-2,2-dicyanoethyl)benzoate and isochromeno[3,4-b]pyrrole derivatives

A novel four-component reaction between 2-formylbenzoic acids, malononitrile, isocyanides, and alcohols has been developed for a highly efficient preparation of alkyl-2-(1-(alkylcarbamoyl)-2,2-dicyanoethyl)benzoate derivatives. This high atom economy reaction led to the construction of two carbon-carbon bonds, one amide, and one ester group in a single synthetic step. Furthermore, a three-component reaction between 2-formylbenzoic acids, malononitrile, and isocyanides in dichloromethane for the preparation of isochromeno[3,4-b]pyrroles has been reported.     

Three-component coupling using arynes and isocyanides: straightforward access to benzo-annulated nitrogen or oxygen heterocycles

A variety of aldehydes, ketones, benzoquinones, or sulfonylimines were found to couple with arynes and isocyanides, giving iminodihydroisobenzofuran or iminoisoindoline derivatives of structural diversity in a straightforward manner. Nucleophilic addition of isocyanides to arynes, a first step of the three-component coupling, was proved to be reversible by the reaction of an unsymmetrical aryne.     

Straightforward access to 2-iminoisoindolines via three-component coupling of arynes, isocyanides and imines

A three-component coupling reaction of arynes, isocyanides and N-tosylaldimines has been developed to offer modest to high yields of diverse 2-iminoisoindolines in one step. Intermediacy of arynes in the coupling has been verified by the reaction of unsymmetrical arynes.     

A novel multicomponent reaction involving isocyanide, dimethyl acetylenedicarboxylate (DMAD), and electrophilic styrenes: facile synthesis of highly substituted cyclopentadienes

Alkyl isocyanides, DMAD, and various activated styrenes furnish fully substituted cyclopentadienes in a one-pot three-component reaction. [reaction: see text]     

An Efficient Synthesis of Trialkyl N-Alkyl-6-methyl-2-pyridone-3,4,5-tricarboxylates

An efficient synthesis of trialkyl N-alkyl-6-methyl-2-pyridone-3,4,5-tricarboxylates from three-component reaction of the zwitterions generated from dialkyl acetylenedicarboxylates and alkyl isocyanides with alkyl 2-chloroacetoacetates is described.     

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.     

An Efficient Synthesis of Trialkyl <Emphasis Type="Italic">N</Emphasis>-Alkyl-6-methyl-2-pyridone-3,4,5-tricarboxylates

Summary. An efficient synthesis of trialkyl N-alkyl-6-methyl-2-pyridone-3,4,5-tricarboxylates from three-component reaction of the zwitterions generated from dialkyl acetylenedicarboxylates and alkyl isocyanides with alkyl 2-chloroacetoacetates is described.     

A three-component reaction involving isocyanide, phosphine and ketenimine functionalities

A three-component reaction involving diphosphinoketenimines, isocyanides and water or ethanol leading to the formation of new five-membered azaphosphaheterocycles is described.     

Synthesis of Ethylenetetracarboxylic Acid Derivatives

Summary. The three-component reaction of the zwitterions generated from dialkyl acetylenedicarboxylate and isocyanides with isocyanates is described. The reaction afforded the corresponding special type of ethylenetetracarboxylic acid derivatives in good yields.     

Ugi three-component reaction of alcohols,amines and isocyanides: A new approach to the synthesis of cyclic amidines

We have developed a novel, simple, efficient and one pot synthetic protocol for the synthesis of cyclic amidines via Ugi three-component reaction of alcohols, amines, and isocyanides.     

Novel isocyanide-based three-component synthesis of 3,4-dihydroquinoxalin-2-amine derivatives

Synthesis of a novel class of highly substituted 3,4-dihydroquinoxalin-2-amine derivatives including spirocyclic compounds from three-component condensation reaction of o-phenylenediamines, diverse carbonyl compounds, and isocyanides in the presence of a catalytic amount of p-toluenesulfonic acid in good to excellent yields at room temperature is described.     

Three-Component Synthesis of Ninhydrin Derived α-Acyloxycarboxamides

A series of ninhydrin derived α-acyloxycarboxamide derivatives were synthesized in good yields in a Passerini three-component reaction by condensation of ninhydrin, carboxylic acids, and isocyanides.     

Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative Agents

An Ugi three-component reaction using preformed α-phosphorated N-tosyl ketimines with different isocyanides in the presence of a carboxylic acid affords tetrasubstituted α-aminophosphonates. Due to the high steric hindrance, the expected acylated amines undergo a spontaneous elimination of the acyl group. The reaction is applicable to α-aryl ketimines bearing a number of substituents and several isocyanides. In addition, the densely substituted α-aminophosphonate substrates showed in vitro cytotoxicity, inhibiting the growth of carcinoma human tumor cell line A549 (carcinomic human alveolar basal epithelial cell).     

A novel, one-pot, three-component synthesis of 4H-pyrido[1,2-a]pyrimidines

A novel, one-pot, three-component synthesis of 4H-pyrido[1,2-a]pyrimidines is described. The reactive 1:1 zwitterionic intermediate, formed by the addition of isocyanides to dialkyl acetylenedicarboxylates, was trapped by N-(2-pyridyl)amides to produce the title compounds under mild reaction conditions in good yields.     

Three-Component Synthesis of Ninhydrin Derived α-Acyloxycarboxamides

Summary. A series of ninhydrin derived α-acyloxycarboxamide derivatives were synthesized in good yields in a Passerini three-component reaction by condensation of ninhydrin, carboxylic acids, and isocyanides.