99657-96-2Relevant 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 (1988)
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: A Novel Synthesis of Pyridazine, Pyrimidine, Pyridine and Pyranopyridine Derivatives
Mohareb, R. M.,Fahmy, S. M.
, p. 664 - 668 (2007/10/02)
Diethyl-3-amino-2-cyano-2-pentendioate (1) reacts with aromatic amines and aminoheterocyclic compounds to yield amide derivatives (2c-h).The latter derivatives were utilised in synthesis of pyridazines (4a, b), pyrimidine (6), pyridone (9) and pyrano4,3-
