On the Reaction between Alkyl Isocyanides and 3-Benzylidene-2,4-pentanedione. A Convenient Synthetic Route to Densely Functionalized Furans

Article abstract of DOI:10.1007/BF00807601

Alkyl isocyanides undergo a formal (1 + 4] cycloaddition reaction with 3-benzylidene-2,4-pentanedione yielding multiply functionalized furan ring systems in fairly high yields. The ¹H NMR spectrum of 4-acetyl -2-(N-benzylamino)-5-methyl-3-pnenylfuran shows an AB pattern for the benzylic methylene protons as a result of a restricted rotation about the bond between the acetyl group and the furan ring, thus giving rise to perpendicular disymmetric planes.