Es. Ratemi et al., PYRIDINE AND PYRIMIDINE RING SYNTHESES FROM 4-(4-MORPHOLINO)-3-PENTENONE AND FROM ETHYL 3-(4-MORPHOLINO)-2-BUTENOATE, Journal of heterocyclic chemistry, 30(6), 1993, pp. 1513-1516
3-Substituted 2(1H)-pyridones are produced from reaction of 4-(4-morph
olino)-3-pentenone 1 with each of the following carbon acids: cyanoace
tamide, malononitrile, cyanothioacetamide, acetylacetamide, benzoylace
tonitrile. Reaction of ethyl 3-(4-morpholino)-2-butenoate 2 with cyano
acetamide gives the corresponding hydroxypyridone. Pyrimidines are for
med by reaction of 1 and of 2 with benzamidine and with S-benzylthio-u
rea; in the last case, the eliminated morpholine displaces the benzylt
hio group to give the final product.