Dodecylphosphonic acid (DPA): a highly efficient catalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions

Kidwai, Mazaahir; Jahan, Anwar; Chauhan, Ritika; Mishra, Neeraj Kumar

doi:10.1016/j.tetlet.2012.01.095

Cited by 58 publications

(14 citation statements)

References 48 publications

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“…Here, we extend our recent efforts to develop efficient catalysts prepared from simple, low cost materials for atom economical and energy efficient organic synthesis [34][35][36][37][38][39], through the design of a MMOF incorporating H3PW12O40 (phosphotungstic acid, PTA) guest molecules to introduce the Brönsted acidity required for one-pot 2H-indazolo[2,1-b]phthalazine-triones synthesis [40][41][42][43]. Chromium(III) terephthalate MOF, MIL-101(Cr) is a promising framework upon which to fabricate such catalysts, since it possesses a high surface area, good thermal and chemical stability, large mesopore channels (∼2.9 and 3.4 nm) and wide pentagonal and hexagonal microporous windows (1.2 and 1.6 nm respectively) which facilitate rapid in-pore transport of substrate and products [15].…”

Section: Introductionmentioning

confidence: 99%

A magnetically-separable H 3 PW 12 O 40 @Fe 3 O 4 /EN-MIL-101 catalyst for the one-pot solventless synthesis of 2H-indazolo[2,1- b ] phthalazine-triones

Hashemzadeh

Amini

Tayebee

et al. 2017

Molecular Catalysis

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A magnetic inorganic-organic catalyst, PTA@Fe3O4/EN-MIL-101 (EN=ethylenediamine, PTA=phosphotungstic acid) was fabricated and characterized by XRD, HRTEM, FESEM, UVVis, TGA-DTA, FT-IR, XPS and porosimetry. PTA retained the parent Keggin structure upon dispersion throughout the amine-functionalized chromium terephthalate metal-organic framework, over which magnetic Fe3O4 nanoparticles were previously introduced. The resulting composite heterogeneous solid acid was an active catalyst for the one-pot synthesis of diverse 2H-indazolo[2,1-b] phthalazine-triones in goodexcellent yields under mild, solventless condition, and offers facile separation and excellent recyclability.

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Section: Introductionmentioning

confidence: 99%

A magnetically-separable H 3 PW 12 O 40 @Fe 3 O 4 /EN-MIL-101 catalyst for the one-pot solventless synthesis of 2H-indazolo[2,1- b ] phthalazine-triones

Hashemzadeh

Amini

Tayebee

et al. 2017

Molecular Catalysis

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“…Figure shows the general procedure for the synthesis of indazolo[1,2‐b]‐phthalazinetrione derivatives. Different substitute on the benzaldehyde include electron withdrawing and electron donating groups was tested with low reaction time, and medium to high yield with compare to literature data . Given data in the Table are the purification yields, and doesn’t mean the reaction yields.…”

Section: Resultsmentioning

confidence: 99%

Waste to wealth: conversion of nano‐magnetic eggshell (Fe₃O₄@Eggshell) to Fe₃O₄@Ca(HSO₄)₂: cheap, green and environment‐friendly solid acid catalyst

Khazaei

Sarmasti

Seyf

2018

Applied Organom Chemis

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Eggshell is a hazardous waste by European Union regulations, so that discarded thousands of tons per year. To convert waste (eggshell) to wealth (catalyst), nano‐magnetic eggshell was prepared based on the nano‐Fe3O4, and then the eggshell was converted to Ca(HSO4)2 with organic acid, namely, chlorosulfonic acid. Based on the back titration, 5.18 mmol SO4H group was loaded per gram of the nano‐structure. Using this method eggshell was converted to cheap, green and environment‐friendly solid acid catalyst. The prepared catalyst (nano‐ Fe3O4@Ca(HSO4)2) was characterized by Fourier transform infrared spectroscopy (FT‐IR), X‐ray diffraction (XRD), energy dispersive X‐ray spectroscopy (EDX), field emission scanning electron microscopy (FE‐SEM), transmission electron microscopy (TEM), vibrating sample magnetometer (VSM), and thermal gravimetric analysis (TGA). The activity of eggshell waste‐derived catalysts was successfully evaluated in the synthesis of value‐added products, namely indazolo[1,2‐b]‐phthalazinetrione derivatives as a benchmark multicomponent reaction. In addition, design of experiments shows that increase in amount of catalyst (and temperature), boost the reaction yield, especially with steeper slope at higher temperature.

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“…This protocol provides a novel and improved method for obtaining 2H-indazolo[1,2-b] phthalazinetriones in terms of good yields with little catalyst loading [87] (Scheme 30). This protocol provides a novel and improved method for obtaining 2H-indazolo[1,2-b] phthalazinetriones in terms of good yields with little catalyst loading [87] (Scheme 30).…”

Section: Indazolophthalazinesmentioning

confidence: 99%

Recent Developments in Chemistry of Phthalazines

El-Azm¹,

Mahmoud²,

Hekal³

2014

Organic Chem Curr Res

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El-Azm et al., Organic Chem Curr Res 2015, 4:1 http://dx.Hydrazines with 2-acyl benzoic acids: Kirill et al. [31] reported the cyclization of 2-nitro-5-chloro phenylhydrazine27 with acyl benzoic acids 28 yielded 2-(2-nitro-5-chlorobenzene)-4-substituted phthalazin-1-ones 29 (Scheme 7).Lukacs and Simig [61] adopted a novel method for the synthesis of phthalazine derivatives 32 via the reaction of benzophenones30 with chromium (VI) oxide in a mixture of acetic anhydride and sulphuric acid followed by cyclization of the products with hydrazine hydrate in refluxing ethanol (Scheme 8).Hydrazine with 1,2-diester:The dimethylphthalate derivative 33 reacted with hydrazine to yield the desired phthalhydrazide34 which undergo chlorination with phosphorus oxychloride to give 35. Subsequent treatment with sodium methoxide afforded the methoxychloride 36 [62] (Scheme 9). Hydrazines with Phthalides: Chloroformylation of 3-methoxy benzoic acid 37 and subsequently radical bromination of 38 produced 39 in good yield. Treatment with triphenyl phosphine gave 40 and wittig olefination with 3,5-dichloro-4-pyridine carboxaldehyde 41 afforded the phthalide 42. Hydrazine cyclization of 42 resulted phthalazine derivative 43 [42] (Scheme 10). Cockcroft et al. [12] synthesized the phthalazinone derivative 47 according the following (Scheme 11). AbstractThis review highlights the methods used for the synthesis of phthalazine derivatives and fused phthalazinones. Their reactivity and synthetic importance were investigated. Phthalazine derivatives can be used as building blocks for heterocycles as well as fused heterocyclic compounds. Scheme 1: Synthesis of phthalazinone derivatives 2 and 5 Scheme 2: Synthesis of phthalazinone derivatives 7-9. Reagents and conditions: (a) CHCl 3 , reflux, 5 h, 51%; (b) hydrazinehydrate, EtOH, addition at rt and then reflux, 90˚C, 2 h, 71%; (c) MeI, KOBu t , DMF, 30 min, 80%; (d) LiOH, THF:MeOH:water (1:1:1), rt, 8-10 h, 81%. Scheme 3: Synthesis of phthalazin(2H)-1-one 11, 12 Scheme 4: Synthesis of 2-[1-(4-oxo-3,4-dihydrophthalazin-1-yl)alkyl]-1Hisoindole-1,3-(2H)-diones Scheme 5: Synthesis of 1,4-disubstituted phthalazinylpiperazine derivatives 21 Scheme 6: One-pot Synthesis of thiadiazinyl-phthalazine-1,4-diones 24 and 26 Scheme 7: Synthesis of 4-substituted phthalazin-1-ones 29. Scheme 8: Synthesis of phthalazine derivatives 32 Scheme 9: Hydrazinolysis of dimethylphthalate derivative 33 Citation: El-Azm FSMA, Mahmoud MR, Hekal MH (2015) Recent Developments in Chemistry of Phthalazines. Organic Chem Curr Res 1:132. Scheme 23: Synthesis of 1H-pyrazolo [1,2-b] phthalazin-5,10-dione derivatives 92 Scheme 24: A plausible mechanism for the synthesis of 1H-pyrazolo[1,2-b] phthalazine-5,10-diones 95 Scheme 25: Synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives 97. Scheme 28: Synthesis of 1-{[(1H-1,2,3-triazol-4-yl)methoxy]phenyl}-1Hpyrazolo[1,2-b] phthalazine-5,10-dione derivatives 104 Scheme 30: Synthesis of 2H-indazolo[1,2-b] phthalazine-triones 107 Scheme 29: Synthesis of 2H-indazolo[2,1-b]pht...

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Dodecylphosphonic acid (DPA): a highly efficient catalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions

Cited by 58 publications

References 48 publications

A magnetically-separable H 3 PW 12 O 40 @Fe 3 O 4 /EN-MIL-101 catalyst for the one-pot solventless synthesis of 2H-indazolo[2,1- b ] phthalazine-triones

A magnetically-separable H 3 PW 12 O 40 @Fe 3 O 4 /EN-MIL-101 catalyst for the one-pot solventless synthesis of 2H-indazolo[2,1- b ] phthalazine-triones

Waste to wealth: conversion of nano‐magnetic eggshell (Fe₃O₄@Eggshell) to Fe₃O₄@Ca(HSO₄)₂: cheap, green and environment‐friendly solid acid catalyst

Recent Developments in Chemistry of Phthalazines

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Dodecylphosphonic acid (DPA): a highly efficient catalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions

Cited by 58 publications

References 48 publications

A magnetically-separable H 3 PW 12 O 40 @Fe 3 O 4 /EN-MIL-101 catalyst for the one-pot solventless synthesis of 2H-indazolo[2,1- b ] phthalazine-triones

A magnetically-separable H 3 PW 12 O 40 @Fe 3 O 4 /EN-MIL-101 catalyst for the one-pot solventless synthesis of 2H-indazolo[2,1- b ] phthalazine-triones

Waste to wealth: conversion of nano‐magnetic eggshell (Fe3O4@Eggshell) to Fe3O4@Ca(HSO4)2: cheap, green and environment‐friendly solid acid catalyst

Recent Developments in Chemistry of Phthalazines

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Waste to wealth: conversion of nano‐magnetic eggshell (Fe₃O₄@Eggshell) to Fe₃O₄@Ca(HSO₄)₂: cheap, green and environment‐friendly solid acid catalyst