Reaction of an isocyanide with an iminium ion intermediate, formed by reaction between 6-formyl-2,3-dimethoxybenzoic acid and secondary amines (dibenzyl-or benzyl(isopropyl)amine) in the presence of silica nanoparticles (silica NPs, ca. 70 nm) proceeds smoothly at room temperature to afford 2,3-dihydro-1H-isoindolone derivatives in high yields.
Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and alkyl acetylenecarboxylates (or ethyl 3-phenyl-2-propynoate), by azathioprine or imidazole leads to vinyltriphenylphosphonium salts, which undergo a Michael addition reaction with a conjugate base to produce phosphorus ylides. Dipotassium hydrogen phosphate, potassium dihydrogen phosphate, and potassium iodide were found to catalyze the conversion of the phosphorus ylides to electron-poor N-vinyl imidazoles in solvent-free conditions under thermal (90 • C, 1 h) conditions. The structural analysis of the products indicated that the reaction is regio-and stereoselective.
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