Mild Synthesis of Fluorosolvatochromic and Acidochromic 3-Hydroxy-4-pyridylisoquinoline Derivatives from Easily Available Substrates.

The reaction of sodium cyanate with benzo[ b]quinolizinium substrates at room temperature gave 3-hydroxy-4-pyridyl-isoquinoline derivatives in good yields. Presumably, the overall reaction proceeds through an ANRORC-type sequence, that is, addition of the nucleophile, ring opening, and ring closure. Preliminary photophysical investigation of the parent compound revealed a pronounced sensitivity of its emission properties toward solvent effects and the pH of the medium.