Substituted pyridopyrimidinones. Part 5. Behavior of 2-hydroxy-4-oxo-4H-pyrido[1,2-α]pyrimidine-3-carbaldehyde in nucleophilic condensation reactions

doi:10.2478/s11696-009-0100-0

Paper

Substituted pyridopyrimidinones. Part 5. Behavior of 2-hydroxy-4-oxo-4H-pyrido[1,2-α]pyrimidine-3-carbaldehyde in nucleophilic condensation reactions

Published Feb 1, 2010 · M. Abass, M. M. Ismail, W. R. Abdel-Monem

Chemical Papers

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10

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0

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Abstract

Reactivity of 2-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (I) towards N- and C-nucleophiles was described. A series of new enaminones II–III, Schiff’s base IV, and hydrazinomethylenediketones V–VIII and X were prepared in good yields. Cyclization of compounds X was achieved by an action of acetic acid to give pyrazolo[3,4-d]pyrido[1,2-a]pyrimidines XI. Base catalyzed Knoevenagel condensation of aldehyde I with some active methyl and methylene compounds led to a series of chalcone-like derivatives XII, XV, XVII, XX, XXIII, XXV, XXVII, XXIX, XXXI, XXXII, and XXXV, in fair yields. Cyclization of enones XII, XV, and XX with hydrazine gave novel heterocyclyl substituted pyrazoles XIII, XVII, and XXI, respectively. Pyrano[2,3-d]pyrido[1,2-a]pyrimidine-2,5-diones XXXIII, XXXIV, and XXXVI derivatives were obtained via cyclization of their respective enone derivatives.

Study Snapshot

This study demonstrates the reactivity of 2-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde towards N- and C-nucleophiles, leading to the synthesis of new enaminones, Schiff's bases

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Substituted pyridopyrimidinones. Part 5. Behavior of 2-hydroxy-4-oxo-4H-pyrido[1,2-α]pyrimidine-3-carbaldehyde in nucleophilic condensation reactions

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