One pot, three-component synthesis of novel 3,4-dihydrophthalazin-2(1H)-yl-4-phenyl-4H-pyrans

Kumar, Pradeep; Reddy, Y. D.; Reddy, Ch. Venkata Ramana; Devi, B. Rama; Dubey, P. K.

doi:10.1016/j.tetlet.2014.02.020

Cited by 20 publications

(7 citation statements)

References 28 publications

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“…The synthesis of the novel pyran-linked phthalazinone-pyrazole hybrids was accomplished by employing an atom economical multicomponent reaction strategy. A phthalazinone derivative, 3-(1,4-dioxo-3,4-dihydrophthalazin-2(1H)-yl)-3-oxopropanenitrile 1 , with an appropriately substituted oxopropanenitrile group that involves in the multicomponent reaction was synthesized from phthalic anhydride and 2-cyanoacetohydrazide ( Kumar et al, 2014 ). The other components employed in this MCR were substituted 1H-pyrazole-5-carbaldehyde 2a and an active methylene–containing compounds.…”

Section: Resultsmentioning

confidence: 99%

Novel Pyran-Linked Phthalazinone-Pyrazole Hybrids: Synthesis, Cytotoxicity Evaluation, Molecular Modeling, and Descriptor Studies

et al. 2021

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A series of novel pyran-linked phthalazinone-pyrazole hybrids were designed and synthesized by a facile one-pot three-component reaction employing substituted phthalazinone, 1H-pyrazole-5-carbaldehyde, and active methylene compounds. Optimization studies led to the identification of L-proline and ethanol as efficient catalyst and solvent, respectively. This was followed by evaluation of anticancer activity against solid tumor cell lines of lung and cervical carcinoma that displayed IC50 values in the range of 9.8–41.6 µM. Molecular modeling studies were performed, and crucial interactions with the target protein were identified. The drug likeliness nature of the compounds and molecular descriptors such as molecular flexibility, complexity, and shape index were also calculated to understand the potential of the synthesized molecules to act as lead-like molecule upon further detailed biological investigations as well as 3D-QSAR studies.

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Section: Resultsmentioning

confidence: 99%

Novel Pyran-Linked Phthalazinone-Pyrazole Hybrids: Synthesis, Cytotoxicity Evaluation, Molecular Modeling, and Descriptor Studies

et al. 2021

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“…At first, we have developed the condensation of diethyl phthalate (1) (1 mmol), ethyl cyanoacetic acid hydrazide 8 (2) (1 mmol) to from 3-(1,4-dioxo-3,4-dihydrophthalazin-(1H)-yl)-3-oxopropanenitrile 17 (3) in the presence of 1ethyl-3-methylimidazolium hydroxide solution [Bmim] The gross structure of this product was assigned on the basis of its spectral data. Furthermore, the compound was supposed to be E-configuration on the presumption that bulky groups in a trans position would confer thermal stability on the molecule.…”

Section: Resultsmentioning

confidence: 99%

[Bmim]OH mediated new synthesis 3-(1H-Indol-3-Yl)Acrylonitrile derivatives

Kesari¹,

Kankala²

2019

ECB

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OH mediated new synthesis of 3-(1H-indol-3-yl)acrylonitrile derivatives 6 have been developed by the reaction of diethyl phthalate (1) with ethyl cyanoacetic acid hydrazide (2) to form 3-(1,4-dioxo-3,4-dihydrophthalazin-(1H)-yl)-3-oxopropanenitrile (3). Then compound 3 reacted with indole-3-aldehyde (4) by Knoevenagel condensation to form compound 2-(1,4-dioxo-1,2,3,4tetrahydrophthalazine-2-carbonyl)-3-(1H-indol-3-yl)acrylonitriles (5). Compounds 5 undergo alkylation with alkylating agents to form 6 with good yields. Compounds 6 could also be synthesized by alkylation of 4 followed by condensation with 3.

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“…The monitoring of the progress of all reactions and homogeneity of the synthesized compounds was carried out and was run using thin layer chromatography (TLC) aluminum sheets silica gel 60 F 254 (Merck). Compounds 1 and 14 were synthesized based on the reported procedures.…”

Section: Methodsmentioning

confidence: 99%

“…The precursor 3-(1,4-dioxo-3,4dihydrophthalazin-2(1H)-yl)-3-oxopropanenitrile (1) was prepared, in a very good yield, from the reaction of equimolar amount of phthalic anhydride with cyanoacetohydrazide in acetic acid at room temperature [30][31][32]. N-coumarinyl phthalazinyl ketones 4 and 5 were prepared from the reaction of 1 and salicylaldehyde either in EtOH containing piperidine at room temprature (RT) or in AcOH containing anhydrous sodium acetate at reflux temperature, respectively.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Novel Heterocycles Utilizing 3‐(1,4‐Dioxo‐3,4‐dihydrophthalazin‐2(1H)‐yl)‐3‐oxopropanenitrile as Precursors

Khidre

Radini

2019

Journal of Heterocyclic Chem

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The reaction of 3‐(1,4‐dioxo‐3,4‐dihydrophthalazin‐2(1H)‐yl)‐3‐oxopropanenitrile 1 and salicyladehyde furnished coumarin derivatives 4 and 5. Coupling reaction of 1 with aryl diazonium chlorides and benzene‐1,4‐bis (diazonium) chloride gave the corresponding hydrazones 6a,b and bishydrazone 9, respectively. Hydrazones 6 underwent intramolecular cyclization upon treating with hydrazine hydrate to give 3‐aminopyrazoles 7. Pyranyl phthalazine 13 was prepared from the reaction of 1 with ethyl 2‐cyano‐3‐ethoxyacrylate 10. Enaminonitrile 14 was reacted with hydrazine hydrate/phenylhydrazine and hydroxylamine to afford the corresponding pyrazoles 16 and oxime 17. The antimicrobial evaluation revealed pyrazole derivatives 7a,b and 16a,b displayed a broad spectrum activity against most strains. 3‐Aminopyrazole derivative 7b showed potent antibacterial activity against all tested microorganisms.

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One pot, three-component synthesis of novel 3,4-dihydrophthalazin-2(1H)-yl-4-phenyl-4H-pyrans

Cited by 20 publications

References 28 publications

Novel Pyran-Linked Phthalazinone-Pyrazole Hybrids: Synthesis, Cytotoxicity Evaluation, Molecular Modeling, and Descriptor Studies

Novel Pyran-Linked Phthalazinone-Pyrazole Hybrids: Synthesis, Cytotoxicity Evaluation, Molecular Modeling, and Descriptor Studies

[Bmim]OH mediated new synthesis 3-(1H-Indol-3-Yl)Acrylonitrile derivatives

Synthesis and Antimicrobial Activity of Novel Heterocycles Utilizing 3‐(1,4‐Dioxo‐3,4‐dihydrophthalazin‐2(1H)‐yl)‐3‐oxopropanenitrile as Precursors

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