Multicomponent Reaction Of Isocyanides Research Articles

Highly Regioselective Assembly of Di‐ or Trisubstituted Pyridines from Arynes, Isocyanides, and 3‐Bromo‐ or 3‐Acetoxypropynes

AbstractA facile synthetic method for the preparation of di‐ and trisubstituted pyridines with high regioselectivity through an intramolecular pericyclization strategy is disclosed. The multicomponent reaction of isocyanides, arynes, and 3‐bromopropyne affords disubstituted pyridines in good yields. In contrast, the use of 3‐acetoxypropyne results in the formation of trisubstituted pyridines through intramolecular pericyclization of an in situ formed azatriene. In this way, desirable pyridines can be constructed in a one‐pot manner.

A three-component reaction of C,N-cyclic N′-acyl azomethine imines, isocyanides, and azide compounds: effective synthesis of 1,5-disubstituted tetrazoles with tetrahydroisoquinoline skeletons

A multicomponent reaction of isocyanides and C,N-cyclic N'-acyl azomethine imines in the presence of TMSCl and NaN3 leads to tetrazole derivatives. These reactions proceeded cleanly to afford the corresponding 1,5-disubstituted tetrazoles containing a tetrahydroisoquinoline skeleton in high to excellent yields.

A multicomponent approach to the synthesis of 1,3-dicarbonylic compounds

A general synthesis of 1,3-dicarbonylic compounds using multicomponent reactions of isocyanides is described. The process involves a Passerini three-component condensation of glyoxal derivatives, isocyanides and acetic acid, followed by metal mediated reductive or solvolytic removal of the acid component. Noteworthy, reductive deacetoxylation of Passerini glyoxylamide adducts was successfully achieved using photochemically activated SmI(2). This procedure constitutes a novel convenient method for the direct synthesis of malonic retro-peptidic subunits.

Reaction of isocyanides with thiophenols and gem-diactivated olefins: a one-pot synthesis of substituted 2-aminopyrroles

A novel multicomponent reaction of isocyanides with thiophenols and gem-diactivated olefins has been discovered. Depending on the choice of isocyanides, substituted 2-aminopyrroles or thioimidates have been prepared. The obtained scaffolds bearing four points of diversity can directly be used in combinatorial syntheses.

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.