One-pot, three-component route to 2H-indazolo[2,1-b]phthalazine-triones

Sayyafi, Maryam; Seyyedhamzeh, Mozhdeh; Khavasi, Hamid Reza; Bazgir, Ayoob

doi:10.1016/j.tet.2008.01.006

Cited by 196 publications

(70 citation statements)

References 21 publications

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“…The reaction is proceed with Knoevenagal condensation between cyclic β-diketone and an aromatic aldehydes in the initial step to from an α,β-unsaturated ketone, which undergoes Michael-type addition with the neucleophilic endocyclic nitrogen of 7H-purin-6-amine under reflux. The adduct is then cyclized intramolecularly with loss of water molecule to give novel phenyl and purine substituted derivatives of quinazolinones (IVa-j) (Scheme 1 & 2) 14 . These reactions have taken place in one flask in a domino manner and the enone system generated in situ immediately undergoes Michael-type addition with 7H-purin-6-amine and subsequent cyclization.…”

Section: Resultsmentioning

confidence: 99%

Novel Phenyl and Purine Substituted Derivatives of Quinazolinones: Synthesis, Antioxidant and Antibacterial Features

2018

Chem Sci Trans

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A one-pot three-component protocol for the preparation of novel phenyl and purine substituted derivatives of quinazolinones through the reaction of 7H-purin-6-amine, cyclohexane-1,3-diketone and aromatic aldehydes in acetic acid is reported. A broad range of quinazolinones were obtained in 55−82% overall yield. In this article, we describe the identification of the good oxidation inhibitors (IC 50 values of 13, 16, 22 and 25 µM, respectively). Compounds IVf and IVg exhibited excellent in vitro radical inhibition activity against a DPPH radical, providing new opportunities for the series. In vitro antibacterial activity toward bacterial strain was also examined, compounds IVb, IVc and IVi exhibits stronger bacterial activity. Overall, the obtained results suggest that further optimization of activity of the series could provide a strong lead for a new antioxidant and antibacterial drug development program.

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Section: Resultsmentioning

confidence: 99%

Novel Phenyl and Purine Substituted Derivatives of Quinazolinones: Synthesis, Antioxidant and Antibacterial Features

2018

Chem Sci Trans

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“…The combined ether extractions were dried over Na 2 SO 4 , concentrated and the residue recrystallized from ethyl acetate/n-hexane (1:3) to afford the pure product. The products 4a-4f are known compounds, and their structures were deduced by comparison of their physical and spectroscopic data with those previously reported [9][10][11][12]. …”

Section: Typical Procedures For the Preparation Of 2h-indazolo [21-b]mentioning

confidence: 88%

“…Therefore, the search continues for a better catalyst for the synthesis of heterocycles containing phthalazine ring fragment in term of operational simplicity, reusability, economic viability, and greater selectivity. Recently the synthesis of 2H-indazolo [2,1-b]phthalazine-triones has been reported by Bazgir and co-workers using p-TSA as catalyst [12].…”

Section: Introductionmentioning

confidence: 99%

Heteropoly Acid in Ionic Liquid - An Efficient Catalyst for the Preparation of 2H-Indazolo[2,1-b]Phthalazine-Triones

Fazaeli¹,

Aliyan²,

Fazaeli³

2010

TOCATJ

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2H-Indazolo[2,1-b]phthalazine-1,6,11(13H)-trione derivatives were synthesized in a simple and efficient method from the three-component condensation reaction of phthalhydrazide, dimedone, and aromatic aldehydes by H 3 PW 12 O 40 in ionic liquid in good to excellent yields and short reaction times. The ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF 4 ) offered the best results in terms of yield of the products. It was observed that a homogeneous reaction medium proved beneficial for the yield of the reaction.

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“…16 Although several reports on the synthesis of phthalazines fused with indazole have been published. [17][18][19][20][21][22][23][24][25][26] However, the development of an efficient and versatile method for the preparation of fused phthalazine with indazole is an active ongoing research area, and there is a potential for further improvement toward green chemistry.…”

mentioning

confidence: 99%

Magnetic Nanoparticle Immobilized N-Propylsulfamic Acid as a Recyclable and Efficient Nanocatalyst for the Synthesis of 2H-indazolo[2,1-b]phthalazine-triones in Solvent-Free Conditions: Comparison with Sulfamic Acid

Rostami

Tahmasbi²,

Yari³

2013

Bulletin of the Korean Chemical Society

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N-Propylsulfamic acid supported onto magnetic Fe 3 O 4 nanoparticles (MNPs-PSA) was used as an efficient and magnetically recoverable catalyst for synthesis of 2H-Indazolo[2,1-b]phthalazine-1,6,11(13H)-trione derivatives from the three-component, one-pot condensation reaction of phthalhydrazide, aromatic aldehydes and cyclic 1,3-diones, in good to excellent yields at 100°C under solvent-free conditions. The catalyst was easily separated with the assistance of an external magnetic field from the reaction mixture and reused for several consecutive runs without significant loss of its catalytic efficiency. In order to compare, the synthesis of 2H-Indazolo[2,1-b]phthalazine-1,6,11(13H)-trione derivatives in the presence of catalytic amount of sulfamic acid (SA) under same reaction condition was also reported.

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One-pot, three-component route to 2H-indazolo[2,1-b]phthalazine-triones

Cited by 196 publications

References 21 publications

Novel Phenyl and Purine Substituted Derivatives of Quinazolinones: Synthesis, Antioxidant and Antibacterial Features

Novel Phenyl and Purine Substituted Derivatives of Quinazolinones: Synthesis, Antioxidant and Antibacterial Features

Heteropoly Acid in Ionic Liquid - An Efficient Catalyst for the Preparation of 2H-Indazolo[2,1-b]Phthalazine-Triones

Magnetic Nanoparticle Immobilized N-Propylsulfamic Acid as a Recyclable and Efficient Nanocatalyst for the Synthesis of 2H-indazolo[2,1-b]phthalazine-triones in Solvent-Free Conditions: Comparison with Sulfamic Acid

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