Synthesis of N-substituted 3-ammomethylidenetetramic acids
(S)-3-(Dimethylamino)methylidene-5-benzyltetramic acid derivatives 4a and 4b were prepared in three steps from N-protected (S)-3-phenylalanines 1a and 1b, respectively. Similarly, N-[N-(benzyloxycarbonyl)glycyl]grycine (1c) was transformed into the enamitione 4c. Acid-catalysed coupling of enaminones 4a-c with aliphatic, aromatic, and heteroaromatic primary amines 5-34 afforded the corresponding N(3′)-substituted 3-aminomethylidenetetramic acid derivatives 35-64 in 29-96% yields. Georg Thieme Verlag Stuttgart.
Pirc, Samo,Bevk, David,Jakse, Renata,Recnik, Simon,Golic, Ljubo,Golobic, Amalija,Meden, Anton,Stanovnik, Branko,Svete, Jurij
p. 2969 - 2988
(2007/10/03)
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