Photocyclization reactions of N-substituted 3-(2- hydroxynaphthalen-1-yl) propenamide derivatives accompanied by liberation of aliphatic and aromatic primary amines

Article abstract of DOI:10.3987/COM-14-12990

(E)-3-(2-Hydroxynaphthalen-1-yl)propenoyl- and (E)-3-(2- hydroxynaphthalen-1-yl)-2-methylpropenoyl-protected aliphatic and aromatic primary amines were synthesized and their photolytic behavior in methanol was explored. The results showed that irradiation of the hydroxynaphthylpropenamide derivatives in a protic polar solvent at wavelengths greater than 280 nm or 340 nm causes rather efficient deprotection reactions to afford the desired amines quantitatively along with fluorescent benzocoumarins.