NITRILES IN ORGANIC-SYNTHESIS - SYNTHESIS OF POLYFUNCTIONALLY SUBSTITUTED PYRIDINE AND BENZENE-DERIVATIVES

1,1,3-Tricyano-2-amino-1-propene (2a) and diethyl 3-amino-2-cyanopent- 2-ene (2b) were allowed to react with a mixture of malononitrile (3a) and acetaldehyde to afford the pyridopyridine derivatives 4a and b. Co mpound 2c reacts with the same mixture to yield the benzene derivative 7. Similarly, 2a reacted with a mixture of acetaldehyde and ethyl cya noacetate (3b) to yield the benzene derivative 8. The pyridine derivat ives 9a-c were obtained from the reaction of 2a-c with a mixture of be nzoylacetonitrile (3c) and acetaldehyde. Similarly 9d and 10 were obta ined from the reaction of 2a and b with a mixture of acetaldehyde and 3d. A mixture of formaldehyde and 3a or 3b reacted with 2b or 2a-c to yield the pyridine derivatives 12 or 13a-c, respectively. Attempts at condensation of 2c with formaldehyde and 3d afford 14 which resulted f rom dimerisation of 2c with loss of ammonia.