SYNTHESIS AND TRANSFORMATIONS OF METHYL (E)-2-(ACETYLAMINO)-3-CYANOPROP-2-ENOATE UND METHYL (E)-2-(BENZOYLAMINO)-3-CYANOPROP-2-ENOATE, VERSATILE REAGENTS FOR THE PREPARATION OF POLYFUNCTIONAL HETEROCYCLIC-SYSTEMS
L. Pizzioli et al., SYNTHESIS AND TRANSFORMATIONS OF METHYL (E)-2-(ACETYLAMINO)-3-CYANOPROP-2-ENOATE UND METHYL (E)-2-(BENZOYLAMINO)-3-CYANOPROP-2-ENOATE, VERSATILE REAGENTS FOR THE PREPARATION OF POLYFUNCTIONAL HETEROCYCLIC-SYSTEMS, Helvetica Chimica Acta, 81(2), 1998, pp. 231-235
Methyl (E)-2-(acetylamino)-3-cyanoprop-2-enoate (2a) and its 2-benzoyl
analog 2b were prepared from the corresponding methyl (Z)-2-(acylamin
o)-3-(dimethylamino)propenoates 1. Multifunctional compounds Z are ver
satile synthons for preparation of polysubstituted heterocyclic system
s such as pyrroles 4, pyrimidines 5 and 6, pyridazines 7, pyrazoles 8,
9, and 11, and isoxazoles 10.