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Pyridine and pyrimidine ring syntheses from 4‐(4‐morpholino)‐3‐pentenone and from ethyl 3‐(4‐morpholino)‐2‐butenoate
Author(s) -
Ratemi Elaref S.,
Namdev Nivedita,
Gibson Martin S.
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300609
Subject(s) - cyanoacetamide , chemistry , morpholino , malononitrile , morpholine , ring (chemistry) , pyrimidine , acetonitrile , combinatorial chemistry , pyridine , medicinal chemistry , organic chemistry , stereochemistry , catalysis , biochemistry , zebrafish , gene
3‐Substituted 2(1 H )‐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.