Pk. Kadaba et Lp. Glavinos, TRIAZOLINES .32 ATTEMPTS AT APPLICATION OF THE STRECKER SYNTHESIS TO HETEROCYCLIC SUBSTITUTED AMINO-ACIDS, Heterocyclic communications, 2(1), 1996, pp. 81-86
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
.