Reaction Of Isocyanides Research Articles

Synthesis of benzoimidazoquinazolines by cobalt-catalyzed isocyanide insertion–cyclization

The synthesis of benzoimidazoquinazoline amines by the reaction of isocyanides and benzo[d]imidazol-anilines via a cobalt-catalyzed isocyanide insertion reaction into the two N–H active bonds is reported.

ChemInform Abstract: Base‐Promoted Cascade Reaction of Isocyanides, Selenium and Amines: A Practical Approach to 2‐Aminobenzo[d][1,3]selenazines under Metal‐Free Conditions.

A new practical approach for constructing 2-aminobenzo[d][1,3]selenazines by base mediated multicomponent reaction of isocyanides, selenium and amines under metal-free conditions is reported. A series of selenazine derivatives are observed in moderate to excellent yields.

Phosphinic acid-promoted addition reaction of isocyanides to (Z)-hydroximoyl chlorides: efficient synthesis of α-(hydroxyimino)amides.

The reaction of (Z)-hydroximoyl chlorides with isocyanides promoted by phosphinic acid in the presence of triethylamine proceeds smoothly to afford α-(hydroxyimino)amides in good to high yields. Phosphinic acid plays an important role in effectively promoting the reaction. A wide range of (Z)-hydroximoyl chlorides and isocyanides were found to be suitable for this reaction.

Synthesis of 2-(3-chromonyl)-2-acyloxycarboxamides via multicomponent reactions of isocyanides

A three-component reaction between a 3-formylchromone, an alkyl isocyanide, and a carboxylic acid which affords novel 2-(3-chromonyl)-2-acyloxycarboxamide derivatives is reported. This cascade reaction sequence represents an atom-economic route to biologically interesting molecules.

Ugi/Himbert Arene/Allene Diels-Alder Cycloaddition to Synthesize Strained Polycyclic Skeleton.

The present work disclosed an efficient multicomponent reaction of isocyanide, allenic acid, aldehyde (ketone), and aniline. This protocol undergoes Ugi reaction followed by an intramolecular arene/allene Diels-Alder sequence, thus providing a rapid access to synthesize strained polycyclic skeletons.

ChemInform Abstract: AlCl3‐Catalyzed O‐Alkylative Passerini Reaction of Isocyanides, Cinnamaldehydes and Various Aliphatic Alcohols for Accessing α‐Alkoxy‐β,γ‐enamides.

The inexpensive Lewis acid AlCl3 was found to be an efficient catalyst for the O-alkylative Passerini reaction of isocyanides, cinnamaldehydes and alcohols. Instead of carboxylic acid in the classical Passerini reaction, alcohols performed both as the solvent and substrate nicely to afford α-alkoxy-amide products in good yield (up to 91%). This method provides practical access for functional α-alkoxy-β,γ-enamide derivatives.

ChemInform Abstract: Palladium‐Catalyzed Insertion Reactions of Isocyanides into Thiocarbamates and Selenocarbamates.

AbstractThe insertion reaction of isocyanides with thiocarbamates and selenocarbamates in the presence of a Pd(0) catalyst gives selectively 2‐oxoethanimidothioates and ‐selenoates, respectively.

ChemInform Abstract: The Long Underestimated Carbonyl Function of Carbohydrates — An Organocatalyzed Shot into Carbohydrate Chemistry

AbstractReview: [38 refs.

ChemInform Abstract: Synthesis of Carbodiimides by I2/CHP‐Mediated Cross‐Coupling Reaction of Isocyanides with Amines under Metal‐Free Conditions.

AbstractBoth symmetric and asymmetric functionalized carbodiimides can be synthesized using the title method.

Nef‐Isocyanide ‐Based One‐pot Two‐step Three Component Dihydrobenzo[4,5]Imidazo[2,1‐b]thiazoles Synthesis

The reactive imidoyl chloride adducts generated in situ from the reaction of isocyanide and acyl chlorides were trapped by 2‐mercaptobenzimidazoles to yield highly functionalized dihydrobenzo[4,5]imidazo[2,1‐b]thiazoles in good yields.

Isocyanide-Based Multicomponent Reactions: Rapid Synthesis of a 5,5-Fused Bicyclic Skeleton from α,β-Unsaturated Ketones and Allenoates

An efficient multicomponent reaction of isocyanides, allenoates, and α,β-unsaturated ketones is disclosed, thus providing rapid access for the synthesis of bicyclic skeletons. From a mechanistic standpoint, the present cycloaddition proceeds through cascade cycloaddition followed by hydration and intramolecular cyclization. Several controlled experiments are also conducted to gain further insight into the reaction mechanism; some valuable and interesting findings were observed during this process. To enrich the structural diversity, 3-(2-oxo­ethylene)indolinones (i.e. with an α,β-unsaturated ketone at position 3) were also found to be compatible in this reaction. In addition, this method is also characterized by its broad substrate scope, mild conditions, and high efficiency, which makes it valuable for further application.

ChemInform Abstract: Synthesis of 4‐Amino‐2‐trifluormethyl Quinoline Derivatives via Palladium‐Catalyzed Cascade Reactions of Isocyanides with N‐(ortho‐Iodo)aryl Enamines.

Abstract A novel efficient synthetic approach to 4-amino-2-trifluormethyl quinoline derivatives is described via palladium-catalyzed cascade reactions of isocyanides with readily available N-(ortho-iodo)aryl enamines under mild conditions. The target heterocycles can be found in many natural products or drugs, which were obtained in generally good to excellent yield.

Synthesis of carbodiimides by I2/CHP-mediated cross-coupling reaction of isocyanides with amines under metal-free conditions.

An I2/CHP-mediated cross-coupling reaction of isocyanides with readily accessible amines via C-N formation is described for carbodiimide synthesis in moderate to excellent yields. This represents a metal-free strategy for a coupling reaction of isocyanides with amines, and it provides an efficient approach for symmetric and unsymmetric functionalized carbodiimide derivative synthesis under mild conditions.

Metal-mediated and metal-catalyzed reactions of isocyanides.

Metal-mediated and metal-catalyzed reactions of isocyanides.

ChemInform Abstract: Chemoselective Addition of Isocyanides to N‐tert‐Butanesulfinimines.

The reaction of isocyanides with N-tert-butanesulfinimines shows remarkable chemoselectivity. β-Sulfinylamino isocyanides are formed exclusively with aromatic sulfinimines, while α-sulfeneimino acetamides result when using aliphatic derivatives. A mechanism is suggested for the latter transformation, together with an explanation for the observed selectivity. Finally, a scope study is presented for this remarkably chemoselective reaction.

ChemInform Abstract: Synthesis of Aminocarbonyl N‐Acylhydrazones by a Three‐Component Reaction of Isocyanides, Hydrazonoyl Chlorides, and Carboxylic Acids.

A novel one-pot multicomponent synthesis of α-aminocarbonyl N-acylhydrazones starting from readily available hydrazonoyl chlorides, isocyanides, and carboxylic acids is reported. The strategy exploits the ability of the carboxylic acid as a third component to suppress all competing reactions between nitrile imines and isocyanides, channeling the course of the reaction toward the formation of this novel class of compounds.

ChemInform Abstract: NiCl2‐Catalyzed Cascade Reaction of Isocyanides with Functionalized Anilines.

Abstract A NiCl 2 -catalyzed isocyanide insertion reaction of anilines bearing another nucleophile functional group utilizing TEMPO as oxidant in isopropyl ethanoate (IPA) or THF has been reported. This simple and general method could afford 2-aminobenzimidazole, 2-aminobenzothiazole, 2-aminobenzoxazole, as well as 2-aminobenzo[ d ][1,3]oxazine in moderate to excellent yields (up to 95% yield).

Synthesis of 4-amino-2-trifluormethyl quinoline derivatives via palladium-catalyzed cascade reactions of isocyanides with N-(ortho-iodo)aryl enamines

A novel efficient synthetic approach to 4-amino-2-trifluormethyl quinoline derivatives is described via palladium-catalyzed cascade reactions of isocyanides with readily available N-(ortho-iodo)aryl enamines under mild conditions. The target heterocycles can be found in many natural products or drugs, which were obtained in generally good to excellent yield.

Palladium-catalyzed Insertion Reactions of Isocyanides into Thiocarbamates and Selenocarbamates

Abstract The insertion reaction of isocyanides with thiocarbamates and selenocarbamates in the presence of a Pd(0) catalyst to selectively give 2-oxoethanimidothioates and -selenoates is reported. This is the first example of the insertion of an isocyanide into a carbon–heteroatom bond using a transition-metal catalyst. DFT calculations suggest that the reaction proceeds through a thiopalladation pathway at the migratory insertion process.

NIS/CHP-mediated reaction of isocyanides with hydrazones: access to aminopyrazoles

A NIS/CHP-mediated reaction of isocyanides with hydrazones to construct aminopyrazoles has been developed.