[TBP]2SO4 ionic liquid catalyst for 4MCR of pyridazinoindazole, indazolophthalazine and pyrazolophthalazine derivatives

Amirmahani, Najmeh; Mahmoodi, Nosrat O.; Malakootian, Mohammad; Pardakhty, Abbas

doi:10.1007/s11030-020-10153-8

Cited by 7 publications

(3 citation statements)

References 40 publications

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Section: Applications Of Pa In Four-component and Pseudo Four-compone...mentioning

confidence: 99%

“…To improve the applicability of the Brønsted acid PEG-SAC catalyst, the authors also examined the preparation of multifunctionalized 1H-pyrazolo[1,2-b]phthalazine-5,10-dione carboxamides in a regio-controlled manner (no 1H-pyrazolo[1,2-b] phthalazine-2-carbonitriles observed) (Scheme 95). 225 Raghavendra Siddaiah performed the domino synthesis of 3amino-1-(1H-indol-2-yl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo [1,2-b]phthalazine derivatives (256) via the reaction of PA (1) with hydrazine hydrate (56), malononitrile (48)/ethyl cyanoacetate (112), and indole-3-carboxaldehydes (255) in the presence of the ionic liquid ([DBUH][OAc]) at 60-65 °C (Scheme 96). 226 Reddy's group in 2014 also obtained 3-amino-1-(1H-indol-2yl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1,2-b]phthalazines (256) in a four-component domino reaction between hydrazine hydrate, N-substituted-indole-3-carboxaldehydes, malononitrile/ethyl cyanoacetate, and dialkylphthalates (methyl and ethyl) in the presence of InCl 3 (30 mol%) in reuxing ethanol within 1 h with 70-85% yield.…”

Section: Applications Of Pa In Twocomponent Reactionsmentioning

confidence: 99%

“…They also achieved phthalazine-diones through the reaction of phthalazine-diones (271) and the reaction of PA (1), aromatic aldehydes (19), hydrazine hydrate (56), and alkyl cyanoacetates (112) (methyl and ethyl) successfully in the same reaction conditions within 15-45 min with 65-92% yield. 255 Some research groups utilized 1,3-cyclohexanedione (273) (in addition with dimedone) to prepare (272) and 3,4-dihydro-1H-indazolo[1,2-b]phthalazine-6,11(2H,13H)-diones (274), which consist of (A). Sadek et al in 2019 developed a highly efficient, catalyst-free, one-pot, multicomponent synthesis of various indazolophthalazines (272,274) in glycerol as a cheap, biodegradable, and commercially available promoting solvent and catalyst under controlled microwave heating (Scheme 105).…”

Section: In Addition Withmentioning

confidence: 99%

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Phthalic anhydride (PA): a valuable substrate in organic transformations

Nikoofar,

Sadathosainy

2023

RSC Adv.

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Section: Applications Of Pa In Four-component and Pseudo Four-compone...mentioning

confidence: 99%

Section: Applications Of Pa In Twocomponent Reactionsmentioning

confidence: 99%

Section: In Addition Withmentioning

confidence: 99%

See 1 more Smart Citation

Phthalic anhydride (PA): a valuable substrate in organic transformations

Nikoofar,

Sadathosainy

2023

RSC Adv.

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One‐pot Multicomponent Synthesis of Novel Chromene Derivatives Using New Organic Phosphate Salt Catalysts

Salmalian,

Mahmoodi,

Sheykhan

2023

ChemistrySelect

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A new method for synthesizing chromene derivatives as an essential class of heterocyclic compounds has been reported. This research described synthesizing and identifying three new organic salt catalysts based on phosphate moieties. Among the synthesized new phosphate‐based organic salt catalysts, disodium ethyl (phenyl) amino phosphate (DSEAP) plays an essential role and reusable catalyst for the preparation of chromene derivatives under different reaction conditions following the principles of green chemistry. Cost‐effectiveness, non‐toxicity and easy availability are among the salient features of this environmentally friendly catalyst. Furthermore, the catalyst was satisfactorily recycled up to four times without significant performance degradation in the yield of synthesized chromenes. X‐ray diffraction (XRD), infrared spectroscopy (FT‐IR), thermal gravimetric analysis (TGA), scanning electron microscopy (SEM), and transmission electron microscopy (TEM) were employed to illustrate the structural and morphologic characteristics of the catalysts. Some synthesized chromene derivatives, including 4I and 4P, showed good antibacterial and biological antioxidant activity compared to the standard drug, respectively. In this research, DSEAP was used as a heterogeneous catalyst in performing one‐pot 3MCRs of aryl aldehyde, an active methylene group e. g. ethyl acetoacetate or diethyl malonate and 5,5‐dimethyl‐1,3‐cyclohexanedione.

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DABCO‐Saccharin Acetate as a Novel, Recyclable and Metal‐Free Catalyst for Eco‐Friendly Synthesis of Various Pyridazino[1,2‐a]indazole and 1H‐indazolo[1,2‐b]phthalazine Heterocycles Under Solvent‐Free Conditions

Pouramiri,

Hadadianpour,

Parhami

2024

ChemistrySelect

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In this research various pyridazino[1,2‐a]indazole and 1H‐indazolo[1,2‐b]phthalazine and 1H‐indazolo[1,2‐b]phthalazine derivatives were produced with a high yield via a multi‐component reaction of dimedone, aldehyde, hydrazine and anhydride compounds in the presence of a novel DABCO‐Saccharin acetate ([DABCOH][Sac‐CH3CO2]) ionic liquid under microwave irradiation. The applied method for producing these heterocyclic compounds demonstrated a number of desirable traits, including quick reactions, high yields of the final product, and straightforward separation of the product and catalyst from the reaction mixture.

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[TBP]2SO4 ionic liquid catalyst for 4MCR of pyridazinoindazole, indazolophthalazine and pyrazolophthalazine derivatives

Cited by 7 publications

References 40 publications

Phthalic anhydride (PA): a valuable substrate in organic transformations

Phthalic anhydride (PA): a valuable substrate in organic transformations

One‐pot Multicomponent Synthesis of Novel Chromene Derivatives Using New Organic Phosphate Salt Catalysts

DABCO‐Saccharin Acetate as a Novel, Recyclable and Metal‐Free Catalyst for Eco‐Friendly Synthesis of Various Pyridazino[1,2‐a]indazole and 1H‐indazolo[1,2‐b]phthalazine Heterocycles Under Solvent‐Free Conditions

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