Synthesis and characterization of 5-(cyclohexylsulfanyl)- 4-aryl-1,2,3-selena/ thiadiazoles

305-309The synthesis and characterization of new 5-(cyclohexylsulfanyl)-4-aryl-1,2,3-selena/ thiadiazoles, obtained from the -sulfanyl semicarbazones are described. The structures of these compounds have been established by ¹H NMR, ¹³C NMR and single crystal X-ray diffraction

Copper(I)-Catalyzed Three Component Reaction of Sulfonyl Azide, Alkyne, and Nitrone Cycloaddition/Rearrangement Cascades: A Novel One-Step Synthesis of Imidazolidin-4-ones

A novel one-pot azide–alkyne/ketenimine–nitrone cycloaddition sequence that is induced by copper(I) and allows the transformation of sulfonyl azides, alkynes, and nitrones to highly substituted imidazolidin-4-ones is described. The corresponding heterogeneous version utilizing Cu(I)-modified zeolites as recyclable heterogeneous catalysts shows marginally improved yield and diastereoselectivity

Copper-Catalyzed Sulfonyl Azide–Alkyne Cycloaddition Reactions: Simultaneous Generation and Trapping of Copper–Triazoles and −Ketenimines for the Synthesis of Triazolopyrimidines

First simultaneous generation and utilization of both copper–triazole and −ketenimine intermediates in copper-catalyzed sulfonyl azide–alkyne cycloaddition reactions is achieved for the one-pot synthesis of triazolopyrimidines via a novel copper-catalyzed multicomponent cascade of sulfonyl azides, alkynes, and azirines. Significantly, the reaction proceeds under very mild conditions in good yields

Copper-Catalyzed Ring-Expansion Cascade of Azirines with Alkynes: Synthesis of Multisubstituted Pyridines at Room Temperature

The first intermolecular ring-expansion cascade of azirines with alkynes for the synthesis of pyridines, enabled by a copper/triethylamine catalytic system via simultaneous generation and utilization of yne-enamine and skipped-yne-imine intermediates, is reported. Experimental as well as computational mechanistic studies revealed that the role of triethylamine is crucial in deciding the reaction pathway toward the pyridine products. This process offers a novel, one-step, direct, and practical strategy for the rapid construction of highly substituted pyridines under exceedingly mild conditions, and an installed alkyne functionality