102266-74-0Relevant articles and documents
Syntheses with Nitriles, LXXIV. - 3-Amino-4,4-dicyano-3-butenoate, a Synthetically Useful Dimer from Malononitrile and Cyanoacetate
Mittelbach, Martin,Junek, Hans
, p. 533 - 544 (2007/10/02)
An improved synthesis of 3-amino-4,4-dicyano-3-butenoate (4) (a codimer from cyanoacetate and malononitrile) is described.The 13C NMR data and pKa value of 4 are compared with those of the isomeric codimer 3 and the dimers 1 and 2.Reaction of 4 with acids or bases leads to the 2(1H)-pyridones 8 and 9, respectively.Conversions of 4 with aldehydes, ketones, and nitroso compounds give the products 11,14, and 15 as well as the benzopyran derivatives 12 and the 2-oxochinoline derivative 13 when using 2-hydroxy- and 2-aminobenzaldehydes. 4 reacts with formamidine to yield the dihydropyrimidine derivative 17 and with sulfur to give the 3,5-diamino-4-cyano-2-thiophenecarboxylates (18).