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

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-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.