Polycyclic Pyrazoles: Routes to New Pyrazoloazines

Hussein, A. M.; El‐Emary, Talaat I.

doi:10.1039/a703809g

Cited by 18 publications

(10 citation statements)

References 6 publications

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“…There are also numerous reports about application of EMCA in synthesis of pyrimidine and pyridine derivatives (108)(109)(110)(111)(112)(113)(114)(115)(116)(117)(118) (Fig. 105-115) [161,222,234,[268][269][270][271]. Some of them were adenosine receptor antagonists [271].…”

Section: Cyclization Via Cyanic Groupmentioning

confidence: 99%

EMCA and DEEM as Michael Reagents Used in Organic Synthesis

Kaczor¹,

Matosiuk

2005

COC

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Section: Cyclization Via Cyanic Groupmentioning

confidence: 99%

EMCA and DEEM as Michael Reagents Used in Organic Synthesis

Kaczor¹,

Matosiuk

2005

COC

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“…They also show miscellaneous biological properties such as virucidal, anticancer, fungicidal, bactericidal and vasodilatory activities [ 21 ]. For all the benefits mentioned above and as part of our program investigating syntheses using pyrazole and fused pyrazoles that have biological importance [ 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 ], we report herein the synthesis of pyrazolo[5,4- b ]pyrimidino[5,4- e ]-pyridinethiones in a one-pot four component environmental friendly method in light of recently reported methods [ 34 , 35 , 36 , 37 ].…”

Section: Introductionmentioning

confidence: 99%

Multi-Component One-Pot Synthesis and Antimicrobial Activities of 3-Methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydro-pyrazolo[5,4-b]pyrimidino[5,4-e]pyridine-5-one and Related Derivatives

El‐Emary

El-Mohsen

2012

Molecules

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The synthesis of 3-methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydropyrazolo[5,4-b] pyrimidino[5,4-e]pyridine-5-one (6) was achieved by two different one-pot multi-component synthesis (one-pot three-component and one-pot four component synthesis). Mono and dialkylation of 6 under different conditions gave compounds 7–11. The hydrazine 12 produced from reaction of 9 with N2H4 was subjected to reactions with some aromatic aldehydes, ethyl acetoacetate, acetyl acetone, ethyl cyanoacetate and triethyl orthoformate to give 13–17, respectively. Compound 12 upon reaction with CS2, nitrous acid, benzoin, chloroacetone and phenacyl bromide gave 18,20,21,22. Alkylation of 18 with ethyl iodide, ethyl chloroacetate and phenacyl bromide gave 19a–c. The antibacterial and antifungal activities of selected derivatives were evaluated.

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“…Pyridone 2 is a potent (4.5 nm), reversible nonpeptidic inhibitor of human leukocyte elastase (HLE) [4,5]. In view of our continued interest in developing efficient synthesis of polyfunctionally substituted heteroaromatics utilizing the readily obtainable starting materials [6][7][8][9], we report here the results of our investigations aiming to explore the synthetic potential of 3-Oxo-N-{4-[(pyrimidin-2-ylamino)sulphonyl]phenyl}butanamide 3 to synthesis of substituted pyridones from enaminone using active methylene reagents. …”

Section: Introductionmentioning

confidence: 99%

β‐Oxoanilides in heterocyclic synthesis: An expeditious synthesis of new polyfunctionally substituted pyridine and pyrazole derivatives

Hussein

Harb

Mousa

2008

Journal of Heterocyclic Chem

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3-Oxo-N-{4-[(pyrimidin-2-ylamino)sulfonyl]phenyl}butanamide 3 was condensed with (DMF-DMA) in refluxing dry dioxane to yield branched structure 4 not its linear isomeric 5. Compound 4 readily reacted with active methylene to yield compounds 8a-c, 14, 17 and 20 respectively. Also enaminone 4 reacted with phenyl hydrazine giving 24 and 25. In contrast, when compound 4 reacted with hydrazine hydrate in the same experimental conditions pyrazole derivative 27 was obtained. Furthermore, condensation of anilide 3 with triethylorthoformate in refluxing acetic anhydride afforded the ethoxy methylene derivative 28. On the other hand, compound 28 was reacted with active methylene reagents, and hydrazines to afford the products identical in all respects (mp., mixed mp., and spectral data) with those corresponding to compounds 6-27 respectively. Similarly, compound 3 was reacted with hydrazine hydrate to afford the reaction product 29. Also, compound 3 reacted with cyanoacetamide in refluxing ethanolic pipridine solution to yield the pyridine derivative 30. Finally, 3 reacted with hydroxylamine hydrochloride in refluxing ethanol/sodium acetate solution to yield the acyclic oxime derivative 31.

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Polycyclic Pyrazoles: Routes to New Pyrazoloazines

Cited by 18 publications

References 6 publications

EMCA and DEEM as Michael Reagents Used in Organic Synthesis

EMCA and DEEM as Michael Reagents Used in Organic Synthesis

Multi-Component One-Pot Synthesis and Antimicrobial Activities of 3-Methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydro-pyrazolo[5,4-b]pyrimidino[5,4-e]pyridine-5-one and Related Derivatives

β‐Oxoanilides in heterocyclic synthesis: An expeditious synthesis of new polyfunctionally substituted pyridine and pyrazole derivatives

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