Abstract
Synthesis of methyl 3-amino-4-carbomyl-2-cyano-2-butenoate is described and2 a classified as a dimer of methyl cyanoacetate and cyanoacetamide. By ammonolysis of the dimer of methyl cyanoacetate with dimethylamine and anilines, resp. the dimethylamide and anilides, resp. (2 b and3 a–j) are obtained. Condensation with salicylaldehyde to the pyrone derivative4 proves the structure of2 a, ring closure reactions in basic or acidic medium yield the pyridones6 a and7 a,b, coupling with diazonium salts the pyridazines8 a–d. The amides2 and the anilides3 show hindered rotation of the enamino- and the amide-group by hydrogen bonds between the nitrogen functions and the ester carbonyl (Z-form). The ΔG ≠ values are reported.
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Junek, H., El Sarhan, T. & Sterk, H. 2-Amino-1-cyan-glutaconsäureamid-1-methylester, ein Dimeres des Cyanessigesters und Cyanacetamid. Monatsh Chem 119, 717–726 (1988). https://doi.org/10.1007/BF00809686
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DOI: https://doi.org/10.1007/BF00809686