Solvent-free synthesis of 5-(aryl/alkyl)amino-1,2,4-triazines and α-arylamino-2,2′-bipyridines with greener prospects

A green and highly efficient method has been developed for the synthesis of 5-(aryl/alkyl)amino-1,2,4-triazines and α-arylamino-2,2′-bipyridines according to the principles of atom economy. It has been performed by two consecutive solvent-free reaction pathways: the ipso -substitution of a cyano-group in 5-cyano-1,2,4-triazines and the aza-Diels-Alder reaction of the resulting 5-arylamino-1,2,4-triazines with 1-morpholinocyclopentene used as a dienophile. Solvent and catalyst-free conditions, operational simplicity, the compatibility with various functional groups, nonchromatographic purification technique, and high yields are the notable advantages of this procedure. The present methodology possesses a low E -factor. A convenient approach towards 5-(aryl/alkyl)amino-1,2,4-triazines and α-arylamino-2,2′-bipyridines was developed following ipso -substitution of a cyano-group by amino groups and, finally, aza-Diels-Alder reaction with 1-morpholynocyclopentene.