Ketenimines and azadienes are transient intermediates in organic chemistry especially in elimination-addition processes and in the formation of heterocyclic systems. These compounds play a considerable role as intermediates in the synthesis of heterocyclic ring systems. In this present research synthesis of novel ketenimines and azadienes via multicomponent reactions (MCRs...

A novel palladium-catalyzed cyclization of bromoacrylamides with isocyanides gives substituted 2,5-diimino-furans, which can be used as the precursor of maleamides. This synthesis likely proceeds, after isonitrile insertion into C–Pd(II) bond, through the coordination of the amide oxygen atom to the Pd(II) centre as a key step.

Palladium-catalyzed oxidative coupling of 2-vinylanilines and isocyanides constitutes a direct, facile, and efficient approach to 2-aminoquinolines. The procedure, employing palladium acetate and silver carbonate, is attractive in terms of assembly efficiency, functional group tolerance, and operational simplicity. A variety of 2-aminoquinolines were prepared in good to excellent yields.

The interaction of imines with isocyanides has been studied. The main product results from a sequential process involving the attack of two units of isocyanide, under Lewis acid catalysis, upon the carbon-nitrogen double bond of the imine to form the 4-membered ring system. The scope of the reaction regarding the imine and isocyanide ranges has been determined, and also some mechanistic variati...

5-Aminopyrazole-4-carbonitrile and ethyl 5-aminopyrazole-4-carboxylate, as potential trifunctional building blocks are introduced in a facile, chemo- and regioselective multicomponent assembly of imidazo[1,2-b]pyrazoles via the Groebke-Blackburn-Bienaymé reaction (GBB reaction). Besides the synthetic elaboration of a green-compatible isocyanide-based access in three-component mode, we describe ...

A transition-metal-free carboxyamidation process, using aryl diazonium tetrafluoroborates and isocyanides under mild conditions, has been developed. This novel conversion was initiated by a base and solvent induced aryl radical, followed by radical addition to isocyanide and single electron transfer (SET) oxidation, affording the corresponding arylcarboxyamide upon hydration of the nitrilium in...

A new reaction model, tandem Michael addition/formal isocyanide insertion into the acyl C-C bond, has been developed. Thus, a series of 2-acylpyrroles and seven-/eight-membered ring fused pyrroles were synthesized from the reaction of methyl isocyanides with enones in a single operation.

A sequential one-pot approach towards N,N'-disubstituted guanidines from N-chlorophthalimide, isocyanides and amines is reported. This strategy provides straightforward and efficient access to diverse guanidines in yields up to 81% through previously unprecedented N-phthaloylguanidines. This protocol also features wide substrate scope and mild conditions.

Efficient access to a large chemical space based on new scaffolds with defined 3D conformations and highly variable in the side chains is needed to find novel functional materials. Four heterocyclic scaffolds based on a four component Ugi reaction of α-amino acids, oxo components, isocyanides and primary or secondary amines suitably functionalized are described. A handful of examples are descri...

The m-terphenyl isocyanides CNAr(Mes2) and CNAr(Dipp2) support five-coordinate, isocyanide/carbonyl monoanions of manganese. For CNAr(Dipp2), a bis-isocyanide anion is available that is remarkably well behaved upon reaction with electrophiles. Most notable is the formation of an unprecedented chloride-substituted metallostannylene.