Studies on the Syntheses of N,N-Dialkyl Neutral Amino Acids and Corresponding N-Oxides
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The N,-N-dimethyl derivatives of neutral amino acids, such as glycine, L-alanine, DL-alanine, L-valine, DL-valine, L-leucine, L-phenylalanine, and L-tyrosine, were prepared by the catalytic reductive condensation of the corresponding amino acids with formaldehyde. The N-oxides were satisfactorily synthesized by the oxidation of the N,N-dimethyl derivatives with an aqueous mixture of hydrogen peroxide and acetic acid. Further studies of the similar condensations of glycine with various aliphatic aldehydes have been investigated. In the case of straight chain aliphatic aldehydes, such as formaldehyde, acetaldehyde, propionaldehyde, and n-butyraldehyde, the corresponding N,N-dialkyl derivatives were obtained. The N-monoalkyl derivative has not been obtained in any case. On the other hand, in the case of aliphatic branched chain aldehydes, such as isobutyraldehyde and isovaleraldehyde, considerable amount of N-monoalkylation has taken place besides the dialkylation. The oxidations of N,N-dialkylglycines to the corresponding N-oxides have been carried out except in the case of N,N-diisobutylglycine.
- 大阪教育大学の論文
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