Synthesis of Methyl (Z)-2-Acetamido-3-aryl-2-butenoates in Two Highly Selective Steps
Diazomethane reacts with methyl (Z)-2-acetamido-3-aryl-2-propenoates regio- and stereospecifically to afford cis-4-aryl-3-acetamido-3-methoxycarbonyl-Δ1-pyrazolines which heated in 1,2-ethanediol at 200 deg C extrude nitrogen to afford stereospecifically methyl (Z)-2-acetamido-3-aryl-2-butenoates in high yields.
Cativiela, C.,Diaz de Villegas, M. D.,Melendez, E.
ON THE SYNTHESIS OF METHYL (Z/E)-2-ACETAMIDO(OR BENZAMIDO)-3-ARYL 2-BUTENOATES
The methyl Z-2-acetamido(or benzamido)-3-aryl-2-butenoates (Z-9a-e, Z-10a-e) were obtained by two alternative procedures: stereospecific opening of Z-2-methyl(or phenyl)-4-(α-arylethylidene)-5(4H)-oxazolones (Z-7a-e, Z-8a-e) and stereospecific homologatio
Cativiela, C.,Villegas, M. D. Diaz de,Melendez, E.
p. 583 - 590
(2007/10/02)
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