Synthesis of Multifunctional Arylated Anilines and Amino‐dihydrophenanthrenes Through Arylacetonitriles Mediated Ring Transformation of 2H‐Pyran‐2‐ones/2‐oxo‐benzo[h]chromenes

Abstract

AbstractWe 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‐oxobenzo[h[chromones 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.