87831-20-7Relevant academic research and scientific papers
Syntheses with Nitriles, LXXIX. Methyl 3-Amino-4-carbomyl-2-cyano-2-butenoate, a Dimer of Methyl Cyanoacetate and Cyanoacetamide
Junek, Hans,Sarhan, El Taher,Sterk, Heinz
, p. 717 - 726 (2007/10/02)
Synthesis of methyl 3-amino-4-carbomyl-2-cyano-2-butenoate is described and 2a 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. (2b and 3a-j) are obtained.Condensation with salicylaldehyde to the pyrone derivative 4 proves the structure of 2a, ring closure reactions in basic or acidic medium yield the pyridones 6a and 7a,b, coupling with diazonium salts the pyridazines 8a-d.The amides 2 and the anilides 3 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(excit.) values are reported. - Keywords: Cyanoacetate; Cyanoacetamide; Dimer
ACTIVATED NITRILES IN HETEROCYCLIC SYNTHESIS. SYNTHESIS OF SEVERAL NEW PYRIMIDINE AND PYRIDAZINE DERIVATIVES.
Sadek,Fahmy,Mohareb,Elnagdi
, p. 101 - 103 (2007/10/02)
Several new pyrimidine, pyridazine, and pyridine derivatives were obtained from 2-(ethoxycarbonyl)-3-aminopentenedinitrile (I) as starting component.
