Pyridine and pyrimidine ring syntheses from 4‐(4‐morpholino)‐3‐pentenone and from ethyl 3‐(4‐morpholino)‐2‐butenoate

Abstract

3‐Substituted 2(1H)‐pyridones are produced from reaction of 4‐(4‐morpholino)‐3‐pentenone 1 with each of the following carbon acids: cyanoacetamide, malononitrile, cyanothioacetamide, acetylacetamide, benzoyl‐acetonitrile. Reaction of ethyl 3‐(4‐morpholino)‐2‐butenoate 2 with cyanoacetamide gives the corresponding hydroxypyridone. Pyrimidines are formed by reaction of 1 and of 2 with benzamidine and with S‐benzylthio‐urea; in the last case, the eliminated morpholine displaces the benzylthio group to give the final product.

Novel Rearrangement of 3‐Acylaminofuro[2,3‐b]pyridines into 3‐(oxazol‐4‐yl)pyridin‐2‐ones

“…NMR data assignment was made using gCOSY, gHSQC, and gHMBC techniques, and VNMR Agilent program (Table ). In 1 H NMR spectra of 1 , the singlets at 5.6–5.9 and 11.5–12.0 ppm corresponded to similar H‐5 and NH signals of 3‐cyano‐4,6‐disubstituted 2(1 H )‐pyridinones .…”