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Synthesis 2005(17): 2969-2988  
DOI: 10.1055/s-2005-916072
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New York

Synthesis of N-Substituted 3-Aminomethylidenetetramic Acids

Samo Pirc, David Bevk, Renata Jakše, Simon Rečnik, Ljubo Golič, Amalija Golobič, Anton Meden, Branko Stanovnik*, Jurij Svete*
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, 1000 Ljubljana, Slovenia
Fax: +386(1)2419220; e-Mail: branko.stanovnik@fkkt.uni-lj.si; e-Mail: jurij.svete@fkkt.uni-lj.si;
Further Information

Publication History

Received 30 May 2005
Publication Date:
23 September 2005 (online)

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Abstract

(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]glycine (1c) was transformed into the enaminone 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.

Key words

amines - chiral pool - coupling - heterocycles - enami­nones

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The final atomic and geometrical parameters, crystal data and details concerning data collection and refinement for both compounds have been deposited with the Cambridge Crystallographic Data Centre as supplementary material with the deposition numbers: CCDC 272155 & 272156, respectively. These data can be obtained, free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html.