Phthalazine-trione Derivatives Research Articles

Magnetic nanoparticles Fe3O4-supported guanidine as an efficient nanocatalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions

Here, the application of guanidine supported on magnetic nanoparticles Fe3O4 (MNPs-guanidine) as a novel magnetically separable base nanocatalyst is described. We have investigated the application of this new catalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives from the three-component, one-pot condensation reaction of phthalhydrazide, cyclic 1,3-dicarbonyl, and aromatic aldehydes under solvent-free conditions. The products were obtained in short reaction times with good to high yields. The supported catalyst could be simply separated and recovered from the reaction mixture with the assistance of an external magnet and reused 18 times with little loss of activity.

Solvent free, Ni-nanoparticle catalyzed greener synthesis and photophysical studies of novel 2H-indazolo[2,1-b] phthalazine-trione derivatives

A nickel nanoparticle (NPs) catalyzed one-pot three component reaction of phthalhydrazide, dimedone and aryl aldehydes under solvent free conditions has been reported. The present approach offers the advantages of simple methodology, clean and mild reaction conditions, short reaction time, low environmental impact, high yield, and excellent purity. The synthesized compounds (2H-indazolo[2,1-b] phthalazine-trione) are found to be suitable candidates for efficient fluorogenic assays to monitor bio-chemical environments.

Proficient synthesis of quinoxaline and phthalazinetrione derivatives using [C8dabco]Br ionic liquid as catalyst in aqueous media

Relatively less toxic and biodegradable ionic liquid [C8dabco]Br has been successfully used for the synthesis of quinoxaline and phthalazinetrione derivatives in an aqueous media. Recyclability of catalyst, high yields, use of environmentally benign aqueous media as solvent, simple product isolation and high atom economy are the noteworthy aspects of the protocols.

Experimental and theoretical study on one-pot, three-component route to 2H-indazolo[2,1-b]phthalazine-triones catalyzed by nano-alumina sulforic acid

A simple, efficient, and high yielding one-pot protocol for the synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives has been developed by three-component coupling of phthalhydrazide, dimedone and some aromatic aldehydes in ecofriendly neat conditions promoted by nano-γ-alumina sulforic acid. This protocol avoids the use of expensive catalysts, toxic solvents and chromatographic separation. Also the proposed protocol was extended to the linear β-diketone (acetylaceton) instead of cyclic diketone (dimedone). The generality and functional tolerance of this convergent and environmentally benign method is demonstrated. The nature of each step of the suggested mechanism for this condensation reaction is also identified through Density Functional Theory (DFT) calculations using B3LYP/6-31G** level of theory. It is shown that the first step is charge controlled; whereas the second one is controlled by frontier molecular orbitals. The 1H and 13C chemical shift values together with the structural parameters of the title compound have been also computed and the scaled values have been compared with the corresponding experimental NMR and X-ray spectra. As a result, the calculated spectroscopic data and optimized geometry show a good agreement with the experimental results.

Alum promoted synthesis of 2H-indazolo(2,1- b)phthalazinetrione derivatives in water

A new and efficient synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione derivatives from the three-component condensation reaction of phthalhydrazide, dimedone, and aromatic aldehydes using alum [KAl(SO4)2.12H2O] as catalyst was performed in aqueous media. The features of this procedure are mild reaction conditions, good to excellent yields, short reaction times and operational simplicity.

Ionic Liquid 4-(3-Methyl-1-imidazolio)-1-butanesulfonic Acid Hydrogen Sulfate-catalyzed Synthesis of Phthalazinetrione Derivatives

A simple method for the synthesis of phthalazinetrione derivatives by a one-pot three-component condensation reaction of phthalhydrazide, 1,3-dicarbonyl compounds and aldehydes catalyzed by the ionic liquid 4-(3-methyl-1-imidazolio)-1-butanesulfonic acid hydrogen sulfate ([BSO3HmIm]HSO4) is reported. Good to excellent yields were obtained in short reaction times in the solvent PEG 600 (polyethylene glycol 600) at 120 °C. The strategy proved to be efficient and environmentally benign. The catalyst/solvent system could easily be recovered and reused for at least 5 times without noticeable loss of activity

Tetrakis(acetonitrile)copper(I) Hexafluorophosphate as an Efficient Catalyst for the Synthesis of Triazolo[1,2-a]indazole-1,3,8-trione and 2Hindazolo[2,1-b]phthalazine-trione Derivatives

Tetrakis(acetonitrile)copper(I) hexafluorophosphate, [Cu(CH3CN)4]PF6, was explored as an efficient catalyst to promote the three-component reaction of aryl aldehydes, dimedone and urazole or phthalhydrazide to afford the corresponding triazolo[1,2-a]indazole-1,3,8-trione and 2H-indazolo[2,1-b]phthalazine-trione derivatives respectively in high yields. The reactions were conducted at 80-100 °C under solvent-free conditions. The catalyst was easily prepared from available and inexpensive materials and was quantitatively recovered from the reaction by simple filtration and reused for a number of cycles with almost consistent activity Keywords: 2H-Indazolo[2, 1-b]phthalazine-trione, dimedone, phthalhydrazide, tetrakis(acetonitrile)copper(I)hexafluorophosphate, triazolo[1, 2-a]indazole-1, 3, 8-trione, urazole, phthalazine, pyrazoles, multi-component, vasorelaxant

Combining click-multicomponent reaction: one-pot synthesis of triazolyl methoxy-phenyl indazolo[2,1-b]phthalazine-trione derivatives

[(1,2,3-Triazol-4-yl)methoxy-phenyl]-2H-indazolo[2,1-b]phthalazine-trione derivatives were synthesized in a simple and efficient method from the one-pot four-component condensation reaction of phthalhydrazide, aromatic propargyloxy aldehydes, active methylene compounds (dimedone and 1,3-cyclohexanedione), and azides in the presence of Cu(OAc)(2)/sodium ascorbate and p-toluenesulfonic acid as catalysts in good to excellent yields.

ChemInform Abstract: Highly Efficient Three‐Component Synthesis of 1H‐Indazolo[1,2‐b]phthalazinetrione Derivatives Catalyzed by Heteropolyacids.

AbstractThe reaction conditions are optimized and a plausible reaction mechanism is proposed.

Highly efficient three-component synthesis of 1H-indazolo[1,2-b]phthalazinetrione derivatives catalyzed by heteropolyacids

Efficient one-pot condensation of aldehyde, dimedone, and phthalhydrazide has been achieved in the presence of a catalytic amount of tungstosilicic acid under solvent-free conditions. A variety of 1H-indazolo- (1,2-b)phthalazinetrione derivatives were prepared in high to excellent yields in short time.

Reusable silica supported poly phosphoric acid catalyzed three-component synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives

An efficient synthesis of 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione derivatives from the three-component condensation reaction of phthalhydrazide, dimedone, and aromatic aldehydes under solvent-free conditions in good to excellent yields and short reaction times using reusable silica supported poly phosphoric acid (PPA–SiO2) as heterogeneous acid catalyst has been investigated.