Substituted pyridopyrimidinones. Part IV. 2-Chloro-4H-pyrido[1,2-a]pyrimidin-4-one as a synthone of some new heterotricycles

doi:10.2298/JSC1001011A

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Substituted pyridopyrimidinones. Part IV. 2-Chloro-4H-pyrido[1,2-a]pyrimidin-4-one as a synthone of some new heterotricycles

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

Journal of The Serbian Chemical Society

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Abstract

Chloro-4H-pyrido(1,2-a)pyrimidin-4-one (1) was utilized as a syn- thone precursor to prepare novel heterotricyclic systems. 2-Azido and 2-hyd- razino derivatives (2 and 3) were obtained by nucleophilic replacement evolving compound 1. The hydrazine derivative 3 was transformed into the azido deriva- tive 2 by nitrosation. Treatment of compound 3 with (bis(methylthio)methyl- ene)malononitrile afforded 2-pyrazolylpyridopyrimidine 4. When compound 1 was reacted with 5-amino-3-(methylthio)-1H-pyrazole-4-carbonitrile, the same compound 4 was obtained with no evidence for the production of (pyrazolyl- amino)pyridopyrimidine 5 or pyrazolodipyridopyrimidine 6. Poly-functionalized dipyridopyrimidine 8 was obtained by reaction of compound 1 with 2-((me- thylthio)-(phenylamino)methylene)propanedinitrile. Cyanoguanidine was reacted with compound 1 to afford N-pyridopyrimidinylguanidine 9, which was subjected to cyclization reaction, in presence of piperidinium acetate, to give pyridopyrimidopyrimidine 10.

Study Snapshot

This study demonstrates the potential of chloro-4H-pyrido(1,2-a)pyrimidin-4-one as a synthone precursor for the preparation of novel heterotricyclic systems.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Substituted pyridopyrimidinones. Part IV. 2-Chloro-4H-pyrido[1,2-a]pyrimidin-4-one as a synthone of some new heterotricycles

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References

Studies on pyrrolopyrimidines as selective inhibitors of multidrug-resistance-associated protein in multidrug resistance.

A novel and selective MRP1 inhibitor, pyrrolopyrimidine (4), shows potential for effective cancer treatment by inhibiting multidrug-resistance-associated protein transport.

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The synthesis of ethyl 5-amino-1-(1-methyl-2-oxoquinolin-4-YL)-3-methylsulfanylpyrazole-4-carboxylate leads to various pyrazolopyrimidines, pyrazolothiazine

Synthesis of pyrazolo[3,4-d]pyrimidine derivatives using ketene dithioacetals

Ketane dithioacetals can be used to synthesize 4-amino- or 4-hydroxy-3-methylthiopyrazolo[3,4-d]pyrimidines with good yields.

Potential ambifunctionality of 2-azidopyrido[1,2-a] pyrimidin-4-one

2-Azidopyrido[1,2-a]pyrimidin-4-one exhibits potential ambifunctionality, forming 1,2,3-triazole derivatives and tetrazolo derivatives under certain conditions.

Substituted pyridopyrimidinones, 1: Convenient PTC alkylation and halogenation of 2-hydroxy-4H-pyrido[1,2-a]pyrimidin-4-one

PTC alkylation and halogenation of 2-hydroxy-4H-pyrido[1,2-a]pyrimidin-4-one under solid-liquid phase transfer catalysis conditions yields various 2-alkoxy products and novel O1,O3-disubstituted glycerol and

Synthesis, antiplatelet and antithrombotic activities of new 2-substituted benzopyrano[4,3-d]pyrimidin-4-cycloamines and 4-amino/cycloamino-benzopyrano[4,3-d]pyrimidin-5-ones.

New 2-substituted benzopyrano[4,3-d]pyrimidin-4-cycloamines and 4-amino/cycloamino-benzopyrano[4,3-d]pyrimidin-5-ones show more potent antithrombotic activity than aspirin

(2-Pyridyl)iminopropadienone

Flash vacuum thermolysis of 2-substituted pyrido[1,2-a]pyrimidin-4-ones generates 2-pyridyl)iminopropadienone, which undergoes thermal elimination of amines to regenerate 2-substituted pyrido

Citations

Simple and Efficient Synthesis of 2‐Oxo‐2H‐Pyrido[1,2‐a]Pyrimidin‐3(4H)‐Ylidene)Acetic Acid and Its Rearrangement in Presence of Acid Media

This efficient one-pot synthesis of 2-[2-oxo-2H-pyrido[1,2-a]pyridmidin-3(4H)-ylidene]acetic acid leads to a seven-membered diazepine with decarboxylation and ring expansion in

Pyrido[1,2-a]pyrimidin-4-ones as antiplasmodial falcipain-2 inhibitors.

Pyrido[1,2-a]pyrimidin-4-ones show excellent inhibitory potential against Plasmodium falciparum cysteine protease falcipain-2, offering potential as antimalarial drugs.

Synthesis of Pyrimidines and Heteroannulated Pyrimidine Ring Systems

Pyrimidines can be synthesized and their heteroannulated ring systems can be formed through Dimroth-type rearrangement, yielding various isomers.