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1.2.3.3.3.4 Four-Component Synthesis of 2-Amino-3-arylpyrroles

DOI: 10.1055/sos-SD-210-00302

Menon, R. S.; Nair, V.Science of Synthesis: Multicomponent Reactions, (20141526.

The four-component reaction of cyclohexyl isocyanide, ammonium acetate, substituted benzaldehydes, and 1,3-dicarbonyl compounds affords 3-aryl-2-(cyclohexylamino)-6,7-dihydro-1H-indol-4(5H)-ones 30 in excellent yields (Scheme 18).[‌22‌] The reaction presumably proceeds through an initial condensation of the 1,3-dicarbonyl compound with the aldehyde followed by interaction of the adduct with ammonium acetate to furnish a 2-benzylidene-3-iminocyclohexanone and a subsequent [4 + 1] annulation of the latter with cyclohexyl isocyanide.

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