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An exception of eschweiler‐clarke methylation: Cyclocondensation of α‐amino amides with formaldehyde and formic acid
Author(s) -
Chen FuLin,
Sung Kuangsen
Publication year - 2004
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570410507
Subject(s) - chemistry , formic acid , formaldehyde , methylation , amide , amino acid , organic chemistry , biochemistry , dna
An exception of Eschweiler‐Clarke methylation was found for α‐amino amides. The α‐amino amides on treatment with formaldehyde and formic acid produce cyclocondensation products, imidazolidin‐4‐ones, but N ‐methylation process becomes important when three substituents of the α‐amino amides are very bulky. On the other hand, N ‐methylation is the only product for Eschweiler‐Clarke methylation of the α‐amino amides with N,N ‐disubstituted amide.