Synthesis of aminonicotinonitriles and diaminopyridines through base-catalyzed ring transformation of 2H-pyran-2-ones

J Org Chem. 2003 Apr 4;68(7):2983-5. doi: 10.1021/jo0204496.

Abstract

An efficient and convenient synthesis of 2-amino-6-aryl-4-methylsulfanylnicotinonitriles (2), 2-amino-6-aryl-4-substituted-aminonicotinonitriles (4), and 2-amino-6-aryl-4-substituted-aminopyridines (6) has been delineated and illustrated through base-catalyzed ring transformation of 6-aryl-3-cyano-4-methylsulfanyl/substituted-amino-2H-pyran-2-ones (1, 3, and 5) with cyanamide and ammonium carbonate separately.