We are reporting a simple and efficient synthesis of highly functionalized aniline by the reaction of 2H‐pyran‐2‐ones and benzyl cyanide in presence of sodamide in dioxane under reflux conditions. Various 4‐sec.amino‐2H‐pyran‐2‐ones, 4‐methylsulfanyl‐2H‐pyran‐2‐ones and 2‐oxobenzohchromones were used as a substrate. Further, synthetic application of obtained arylated aniline was carried out to afford multifunctional carbazoles (13). 2′′‐Bromo‐1,1′ : 2′,1′′‐teraryl‐3′‐amines (6) and 4‐(2‐bromoarylyl)‐9,10‐dihydrophenanthren‐3‐amines (11) was used to demonstrate the the synthesis of carbazoles. The structure of isolated product 11 d was ascertained by spectroscopic and single crystal X‐ray diffraction analyses. We have explained the role of nonpolar solvents in the synthesis of arylated aniline. Sodamide‐mediated synthesis of arylated anilines in nonpolar solvent 1,4‐dioxane is reported. Functionalized carbazoles were also afforded from suitably functionalized arylated anilines.