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- W2953019497 abstract "Azidation of the chloroaldehyde 2, which was obtained from the 6-hydroxy-2-pyridones 1, afforded the 6-azido-2-pyridones 3. Compound 3 can be converted to the corresponding 6-amino-2-pyridones 5, by the reaction with triphenylphosphine via phosphazenes and subsequent hydrolysis (Staudinger reaction). This obtained amine 5 reacts with ethyl cyanoacetate in an ethanolic solution containing piperidine to give 7-amino-6-carbethoxy-3-cyano-1,4-dimethyl-1,8-naphthyridin-2(1H)-one (9). Reaction of 9 with dimethylformamide dimethyl acetal, triethylorthoformate and hydrazine hydrate furnished the new 1,8-naphthyridin-2-ones 10, 11 and 12, respectively, in good yields. On the other hand, refluxing 9 with piperidine or morpholine, as secondary amines, did not afford the corresponding 1,8-naphthyridin-2-ones 13, but instead it undergoes a thermal decomposition under these reaction conditions to yield the unexpected 6-amino-3-cyano-1,4-dimethyl-pyridin-2(1H)-one (14)." @default.
- W2953019497 created "2019-06-27" @default.
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- W2953019497 date "2001-01-01" @default.
- W2953019497 modified "2023-09-23" @default.
- W2953019497 title "A New Approach to the Synthesis of Polyfunctionally Substituted 1,8-Naphthyridin-2-one Derivatives from 6-Azidopyridones: A Novel Thermal Decomposition to 6-Aminopyridones" @default.
- W2953019497 doi "https://doi.org/10.1055/s-2001-9749" @default.
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