Reaction Of Isocyanides Research Articles

Synthesis of fully substituted pyrano[2,3- c]pyrazole derivatives via a multicomponent reaction of isocyanides

The three-component reaction of the zwitterions generated from dialkyl acetylenedicarboxylate and isocyanides with 3-methyl-1-phenyl-1 H-pyrazol-5(4 H)-one is described. The reaction afforded the corresponding special type of fully substituted pyrano[2,3- c]pyrazole derivatives in good yields without using any catalyst and activation.

Reaction of isocyanides with a molybdenum complex containing a tridentate silyl-phosphine ligand: the Si ligand effect on site preference of the isocyanide ligands

A molybdenum trihydride complex containing a tridentate silyl-phosphine ligand reacts with isocyanides to give isocyanide complexes, in which the Si atom and the isocyanides are cis to each other; the preferred configuration in the resulting complexes is reasonably explicable provided the Si fragment is acting as a good pi-acid ligand.

GaCl3- and TiCl4-Catalyzed Insertion of Isocyanides into a C−S Bond of Dithioacetals

The insertion reaction of isocyanide into a C-S bond of dithioacetals is catalyzed by GaCl3 or TiCl4 to afford thioimidates containing an alpha-alkylthio group. Balanced thiophilicity of these Lewis acids is critical for efficient catalysis.

Isocyanide Ligands Adsorbed on Metal Surfaces: Applications in Catalysis, Nanochemistry, and Molecular Electronics

Knowledge of the coordination chemistry and reactivity of isocyanide ligands in transition-metal complexes forms the basis for understanding the adsorption and reactions of isocyanides on metal surfaces. In this overview, we explore reactions (often catalytic) of isocyanides adsorbed on metal surfaces that reflect their patterns of reactivity in metal complexes. We also examine applications of isocyanide adsorption to the stabilization of metal nanoparticles, the functionalization of metal electrodes, and the creation of conducting organic-metal junctions in molecule-scale electronic devices.

ChemInform Abstract: Efficient Synthesis of Functionalized 2,5‐Dihydrofurans and 1,5‐Dihydro‐2H‐pyrrol‐2‐ones by Reaction of Isocyanides with Activated Acetylenes in the Presence of Hexachloroacetone.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Stereoselective Synthesis of dialkyl 2-benzoyloxy-3-(N-alkyl-N‘-arylcarbamimidoyl)succinates: A Four Component Reaction

An improved four-component reaction of isocyanides is described. The reaction between alkyl isocyanides, dialkyl acetylenedicarboxylates, aromatic amines and benzoic acid in dichloromethane at room temperature leads to dialkyl 2-benzoyloxy-3-( N-alkyl- N′-arylcarbamimidoyl)succinates in good yields

A simple and efficient approach to the synthesis of 4 H-furo[3,4- b]pyrans via a three-component reaction of isocyanides

A three-component reaction of an isocyanide, a dialkyl acetylenedicarboxylate, and tetronic acid in dichloromethane at room temperature afforded 4 H-furo[3,4- b]pyran derivatives. These compounds are closely related with ring systems, TAN-2483B, TAN-2483A, and FD-211 which have a broad spectrum of biological activity.

Efficient synthesis of functionalized 2,5-dihydrofurans and 1,5-dihydro-2H-pyrrol-2-ones by reaction of isocyanides with activated acetylenes in the presence of hexachloroacetone

Isocyanides react smoothly with dimethyl acetylenedicarboxylate in the presence of hexachloroacetone to produce dimethyl 5-[alkyl(aryl)imino]-2,2-bis(trichloromethyl)-2,5-dihydro-furan-3,4-dicarboxylates in high yields. When the reaction was performed with dibenzoylacetylene, 3-benzoyl-1-alkyl-4-chloro-5-hydroxy-5-phenyl-1,5-dihydro-2H-pyrrol-2-ones were obtained.

ChemInform Abstract: Novel Synthesis of Dihydrothiophene‐2,5‐diimine Derivatives by the Three‐Component Reaction of Isocyanides with Enamines and Arylisothiocyanates.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: One‐Pot Synthesis of Functionalized Keteneimines by Three Component Reaction of Isocyanides, Dialkyl Acetylenedicarboxylates, and 4‐Phenylaminocoumarin.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A novel three-component reaction for the synthesis of 1,2-dihydroisoquinolines via the reaction of isoquinoline and isocyanides with strong CH-acids in water

A straightforward and efficient method for the synthesis of 1,2-dihydroisoquinolines via the one-pot, three-component reaction of an isocyanide, isoquinoline and a strong CH-acid in water without using any catalyst at 70 °C is reported. The method offers several advantages including high yields of products and an easy work-up procedure.

One-pot Synthesis of Functionalised Keteneimines by three Component reaction of Isocyanides, Dialkyl acetylenedicarboxylates, and 4-phenylaminocoumarin

The reactive intermediate generated by the reaction of alkyl isocyanides and dialkyl acetylenedicarboxylates was trapped by 4-phenylaminocoumarin to produce dialkyl 2-cyclohexylamino-5-oxo-4 H,5 H-pyrano[3,2- c]chromene-3,4-dicarboxylates in good yields.

Synthesis of Functionalized 5‐Imino‐2,5‐dihydro‐furans Through the Reaction of Isocyanides with Activated Acetylenes in the Presence of Ethyl Bromopyruvate.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Non-nanogold Catalysis of Reactions of Isocyanides, Secondary Amines, and Oxygen to Give Ureas

Although numerous studies show that supported nanogold particles (<5 nm) catalyze a variety of reactions, the results presented in this paper show that unsupported bulk gold powder (∼1000 nm particle size), which is generally known to be a poor catalyst, catalyzes the reactions of isocyanides (R−N⋮C), secondary amines (HNR‘2), and O2 to give ureas OC(NHR)(NR‘2) under mild conditions (60 °C, 1 atm O2). Kinetic studies are consistent with a proposed mechanism.

Novel Synthesis of Dihydrothiophene-2,5-diimine Derivatives by the Three-Component Reaction of Isocyanides with Enamines and Arylisothiocyanates

A distribution of the products in the reaction of aryl isothiocyanates with isocyanides and 2,2-dialkylenamines has been studied in details. In range 55-60 °C this reaction results in the formation of dihydrothiophene-2,5-diimine derivatives, constitutions of which are proved by an X-ray analysis. In contrast at high temperature (above 110 °C) the major products in the present reaction are 2-imino-5-thiopyrrolidones. A one step pathway to dihydrothiophene structure has been elaborated.

Synthesis of Novel Heterocyclic Structures via Reaction of Isocyanides with s‐trans‐Enones.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Highly Selective Double Chalcogenation of Isocyanides with Disulfide−Diselenide Mixed Systems

A highly selective method for introducing thio and seleno groups into a variety of isocyanides has been developed based on the elucidation of the relative reactivities of organic dichalcogenides and chalcogen-centered free radicals. When the reactions of aromatic isocyanides (ArNC) with organic disulfides (R'SSR') and diselenides (R''SeSeR'') are conducted upon irradiation with a tungsten lamp through Pyrex (hnu>300 nm), simultaneous introduction of both thio and seleno groups into the isocyanides takes place to provide the corresponding thioselenation products (R'S-C(=NAr)-SeR'') in good yields with excellent selectivity. In the cases of aliphatic isocyanides (RCN), a novel diselenide-assisted bisthiolation of RNC with diaryl disulfides (Ar'SSAr') proceeds successfully to give the corresponding bisthiolation products (Ar'S-C(=NR)-SAr'), although the same photoirradiated reaction of RNC with diaryl disulfides does not occur in the absence of diselenide. These double chalcogenation reactions are assumed to proceed via the formation of imidoyl radical intermediates by the reaction of isocyanides with relatively reactive thio radicals (compared with seleno radicals). The obtained thioselenation products can be employed as useful precursors for the construction of beta-lactam framework by the formal [2+2] cyclization with ketene equivalents.

One-pot three-component reaction of isocyanides, dialkyl acetylenedicarboxylates and phthalhydrazide: synthesis of highly functionalized 1 H-pyrazolo[1,2- b]phthalazine-5,10-diones

Protonation of the highly reactive 1:1 intermediate produced in the reaction between alkyl isocyanides and electron-deficient acetylenic esters with phthalhydrazide, leads to a vinylisonitrilium cation, which undergoes an addition reaction with the conjugate base of the phthalhydrazide to produce dialkyl 3-(alkylamino)-5,10-dioxo-5,10-dihydro-1 H-pyrazolo[1,2- b]phthalazine-1,2-dicarboxylates in fairly good yields at room temperature.

Shaken Not Stirred: A Facile Synthesis of 1,4‐Bis(furo[2,3‐d]pyrimidine‐2,4(1H,3H)‐dione‐5‐yl)benzenes by One‐Pot Reaction of Isocyanides, N,N′‐Dimethylbarbituric Acid, and Terephthaldialdehyde.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Synthesis of functionalized 5-imino-2,5-dihydro-furans through the reaction of isocyanides with activated acetylenes in the presence of ethyl bromopyruvate

The reaction between alkyl(aryl) isocyanides and dibenzoylacetylene in the presence of ethyl bromopyruvate leads to ethyl 3,4-dibenzoyl-2-bromomethyl-5-alkyl(aryl)imino-2,5-dihydro-furan-2-carboxylates in high yields. Dialkyl acetylenedicarboxylates react with tert-butyl isocyanide and ethyl bromopyruvate to produce 3,4-dialkyl 2-ethyl 2-bromomethyl-5-tert-butylimino-2,5-dihydro-furan-2,3,4-tricarboxylates.