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Published on: August 16, 2018
Elusive 2-aminofuran Diels-Alder substrates for a straightforward synthesis of polysubstituted anilines
Ana G Neo1, Ana Bornadiego, Jesús Díaz
1Laboratorio de Química Orgánica y Bioorgánica (L.O.B.O.), Dept. Química Orgánica e Inorgánica, Facultad de Veterinaria, Universidad de Extremadura, 10071 Cáceres, Spain. cfernan@unex.es.
Abstract:
The first multicomponent coupling of isocyanides, α,β-unsaturated carbonylic compounds and dienophiles, based on the trapping of unstable intermediate 2-aminofurans, is described. This novel tandem [4 + 1]-[4 + 2] cycloaddition is efficiently catalysed by yttrium triflate and constitutes an operationally simple and highly convergent approach to a variety of polysubstituted anilines. Moreover, this methodology permits the use of tert-butylisocyanide as a convertible isocyanide to yield directly N-unprotected anilines in the same pot.
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