Substituted 2-aminonicotinonitriles

Article abstract of DOI:10.1002/ardp.19943270205

Aminolysis of the cyanoketene-O,N-acetal 1 Z/E with the amines 2a,b leads to the E-configurated cyanoketeneaminals 3a,b. Compounds 3a,b are reacted with 1,3-biselectrophiles 4, 6a,b, 9 HCl, 12, 13, 15a,b, 17, and 19 to yield the N²-substituted 2-aminonicotinonitriles 5, 7, 8, 10, 11, 14, 16, and 20. Reaction of some 2-aminonicotinonitriles with an α-phenylethyl substituent in position 2 (14b, 16a, 8a, 20b, 5 and 8b) with PPA leads to the primary 2-aminonicotinonitriles 21a-f.