TRIAZOLINES .32 ATTEMPTS AT APPLICATION OF THE STRECKER SYNTHESIS TO HETEROCYCLIC SUBSTITUTED AMINO-ACIDS

The Strecker synthesis provides a versatile route to the synthesis of both aliphatic and aromatic amino acids. It involves the formation of an a-amino nitrile by the addition of hydrogen cyanide to an aldimine, followed by acid hydrolysis of the nitrile to yield the amino acid. H owever, the Strecker method fails when applied to the synthesis of a 4 -pyridyl substituted heterocyclic amino acid, and yields instead 4-pyr idinecarboxanilide as the reaction product. These results indicate tha t the Strecker synthesis is not a useful route for the preparation of amino acids bearing electron withdrawing groups, such as the 4-pyridyl .