Multiple Isocyanide insertions promoted by protic and Lewis acids

Tetrahedron Chem, Journal Year: 2023, Volume and Issue: 9, P. 100056 - 100056

Published: Dec. 9, 2023

Complexation of Lewis acids to electrophiles triggers the sequential insertion two or more isocyanides resulting in valuable iminonitriles heterocycles. The number insertions is controlled by nature alkyl- arylisocyanide and presence a proximal nucleophile capable attacking intermediate nitrilium; loss an alkyl group from nitrilium attack terminates further isocyanide insertions. mechanistic survey protic acid-promoted aims provide fundamental understanding reactivity selectivity facilitate synthetic applications. review structured with introductory overview followed analysis before moving double insertions, which are most prevalent, then triple insertions; concludes sole example quadruple insertion. hope that insight contained will aid applying acid-activated prepare array complex

Language: Английский

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Synthesis of N-fused polycyclic indoles via a Pd-catalyzed multicomponent cascade reaction consisting of an amide-directed [3+1+1] annulation reaction of 3-diazo oxindole and isocyanides

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(6), P. 2639 - 2648

Published: Jan. 1, 2024

A palladium-catalyzed and amide-assisted multicomponent reaction of 3-diazo oxindole, isocyanide, water to generate biologically important oxazole-fused indole scaffolds has been reported.

Language: Английский

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Synthesis of β-Carbonyl α-Iminoamides by Double Insertion of Isocyanides into Aldehydes

Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6335 - 6340

Published: July 24, 2024

An unprecedented trimethylsilyl trifluoromethanesulfonate (TMSOTf)-promoted selective double insertion of isocyanides into aldehydes was developed, providing an efficient protocol for synthetically challenging β-carbonyl α-iminoamides. The given approach is applicable a diverse selection readily accessible aldehydes, along with serving as essential precursors "amide" and "imine" scaffolds. versatile transformations the products were demonstrated, pivotal intermediates plausible mechanism identified.

Language: Английский

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Nickel-catalyzed cyclization of alkynyl nitriles with isocyanide: An expedient way to the synthesis of polysubstituted pyrroles

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 146, P. 155194 - 155194

Published: July 9, 2024

Language: Английский

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