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- W623761008 abstract "'The catalytic reductive condensations of neutral amino acids, such as glycine, L-alanine, L-valine, L-leucine, L-phenylalanine, and L-tyrosine, with formaldehyde using Raney nickel catalyst have been investigated. The N, N-dimethyl derivative was obtained in each case except in the case of L-phenylalanine. However, in the case of L-phenylalanine, considerable N-monomethy]ation took place besides the N-dirnethylation. The similar reactions of glycine with various aliphatic aldehydes, such as propionaldehyde, n-butyraldehyde, isobutyraldehyde, and isovaleraldehyde, give the corresponding N-monoalkyl derivatives. These results shoW the bulkiness of the substituent of aldehydes inhibits the condensation reaction of the N-monoalkyl glycine initially formed and the aldehyde. In the previous papers, the catalytic reductive-N, N-dimethylations of various neutral amino acids,i) and acidicamino acids2) using silk-palladium catalyst were investigated. The similar reductive alkylation of glycine with various aliphatic aldehyde was also studied.3) In the present study, the reductive condensation of various neutral amino acids with aqueous formaldehyde using Raney nickel catalyst have been investigated. In the case of silk-palladium catalyst, the results obtained apparent!y indicate that the corresponding N, N-dialkyl derivatives were obtained as the a!kylation products when aliphatic straight chain aldehydes were employed in these reactions. The N-monoalkyl derivatives initially formed seem to be more reactive to the carbonyl residue of the aldehydes and readily react with an excess of aldehydes to give the corresponding N,N-dialkyl derivatives. On the other hand, in the case of the reductive alkylation of glycine with aliphatic branched chain aldehydes, such as isobutyraldehyde and isovaleraldehyde, considerable monoalkylation took place besides the dialkylation. However, when an excess of the :aldehyde was used, the N,N-dialkyl derivative was obtained in a nearly quantitative yield. These results show the bulkiness of the substituent of aliphatic branched chain aldehydes considerably inhibits the condensation reaction of the N-monoalkyl glycine initial!y formed and the aldehyde. In the course of the reaction, the silk-palladium catalyst showed no reductivity in responce to excess of any aldehyde." @default.
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- W623761008 date "1972-03-01" @default.
- W623761008 modified "2023-09-23" @default.
- W623761008 title "The Catalytic Reductive Condensation of Neutral Amino Acids with Various Aliphatic Aldehydes using Raney Nickel Catalyst" @default.
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