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

Author:

Rana Shally12,Althagafi Ismail3,Chahal Mohit1,Pratap Ramendra1ORCID

Affiliation:

1. Department of Chemistry University of Delhi Delhi 110007- India

2. Department of Chemistry, School of Science Indrashil University, Rajpur, Kadi, Ahmedabad-Mehsana Highway Gujarat 382740 India

3. Department of Chemistry College of Applied Science, Umm Al-Qura University Makkah Saudi Arabia

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 11d 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.

Funder

University of Delhi

Publisher

Wiley

Subject

General Chemistry

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