Phosphorus mediated cyclisation of a β-arylaminoacrylamide to a quinoline: A simple synthesis of SKandF 96067

Article abstract of DOI:10.1016/0040-4039(95)01578-6

The reversible (H⁺/K⁺)ATPase inhibitor SKandF 96067 1 was prepared in two steps from Meldrun's Acid by cyclisation of the acrylamide 4 with Ph₃P/C₂Cl₆/Et₃N. Evidence for the formation of imidoylketene imine 3 was obtained by trapping with phenyl isocyanate. Thermal degradation of an amidine such as 12 also gave SKandF 96067 1.