Zeitschrift für Naturforschung B, A journal of chemical sciences
Rok Šinkovec, Uroš Grošelj, Benjamin Prek, Marta Počkaj, Sebastijan Ričko, Jurij Svete, Branko Stanovnik
In this communication, a simple synthesis of dimethyl 2-[(Z)-3-amino-1-oxo-1-(substituted)but-2-en-2-yl]fumarates is described. Methyl ketones were transformed by treatment with N,N-dimethylacetamide dimethyl acetal (DMADMA) into 3-dimethylamino-1-(substituted)but-2-en-1-ones, followed by treatment with ammonium acetate into (Z)-3-amino-1-(substituted)but-2-en-1-ones and addition to dimethyl acetylenedicarboxylate. These novel polysubstituted butadienes are potential intermediates for the metal-free preparation of polysubstituted five- and six-membered heterocycles.
Read article: Z. Naturforsch., 2016, 71, 677-682