Synthesis of pseudo-indoxyl derivatives via sequential Cu-catalyzed S(N)Ar and Smalley cyclization.

ortho-Bromophenyl sec-alkyl/sec-alkenyl ketones, on reaction with sodium azide in the presence of copper salts, undergo sequential SNAr followed by Smalley cyclization to provide pseudo-indoxyl derivatives. Some of these pseudo-indoxyl derivatives exhibit interesting fluorescent properties and broad Stokes shifts.