Design and synthesis of nickel tetra‐2,3‐pyridiniumporphyrazinato trinitromethanide as an influential catalyst and its application in the synthesis of 1,2,4-triazolo based compounds

Dashteh, Mohammad; Baghery, Saeed; Zolfigol, Mohammad Ali; Khazaei, Ardeshir; Makhdoomi, Sajjad; Safaiee, Maliheh; Rakhtshah, Jamshid; Bayat, Yadollah; Asgari, Asiye

doi:10.1016/j.jpcs.2021.110322

Cited by 8 publications

(4 citation statements)

References 38 publications

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“…To continue our investigations in this field [65][66][67][68][69][70] , herein, we synthesized numerous pyrimidine-6-carbonitrile, pyrimidin-5-one, and tetrahydroquinoline-3-carbonitrile compounds via a cooperative geminal-vinylogous anomeric based oxidation under solvent-free conditions at 100 °C (Fig. 2) by using oxovanadium(V)-[5,10,15,20tetrakis(pyridinium)-porphyrinato]-tetra(tricyanomethanide) [(VO)TPP][(TCM) 4 ] as a versatile catalyst (Fig.…”

Section: Synthesismentioning

confidence: 96%

Synthesis of pyrimidine-6-carbonitriles, pyrimidin-5-ones, and tetrahydroquinoline-3-carbonitriles by new superb oxovanadium(V)-[5,10,15,20-tetrakis(pyridinium)-porphyrinato]-tetra(tricyanomethanide) catalyst via anomeric based oxidation

Dashteh

Makhdoomi

Baghery

et al. 2022

Sci Rep

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Oxovanadium(V)-[5,10,15,20-tetrakis(pyridinium)-porphyrinato]-tetra(tricyanomethanide) [(VO)TPP][(TCM)4] was designed, synthesized and characterized by various techniques such as FT-IR, EDX, SEM equipped with EDX mappings, CHN elemental analysis, ICP-OES, XRD, SEM, TEM, TGA, DTA, DRS, Kubelka–Munk function (Tauc’s plot), and UV–Vis analyses. Then, [(VO)TPP][(TCM)4] was used as a benign and expedient catalyst for the synthesis of numerous heterocyclic compounds such as 5-amino-7-(aryl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles, 5-amino-7-(aryl)-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles, 7-(aryl)-7,12-dihydro-5H-isochromeno[4,3-d][1,2,4]triazolo[1,5-a]pyrimidin-5-ones, and 4-(aryl)-2-(1H-indol-3-yl)-5,6,7,8-tetrahydroquinoline-3-carbonitriles under solvent-free conditions at 100 °C via a cooperative geminal-vinylogous anomeric based oxidation.

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Section: Synthesismentioning

confidence: 96%

Synthesis of pyrimidine-6-carbonitriles, pyrimidin-5-ones, and tetrahydroquinoline-3-carbonitriles by new superb oxovanadium(V)-[5,10,15,20-tetrakis(pyridinium)-porphyrinato]-tetra(tricyanomethanide) catalyst via anomeric based oxidation

Dashteh

Makhdoomi

Baghery

et al. 2022

Sci Rep

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“…There are publications describing the use of various other green catalysts for the synthesis of triazoloqiunolinones: e. g., nickel tetra-2,3-pyridiniumporphyrazinato trinitromethanide, [131] p-toluenesulfonic acid monohydrate, [132] anthranilic acid, [133,134] trimethyl amine N-oxide [135] and other.…”

Section: Reactions Of Aminotriazolesmentioning

confidence: 99%

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Desenko,

Gorobets,

Lipson

et al. 2023

The Chemical Record

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Dihydroazolopyrimidines are an important class of heterocycles that are isosteric to natural purines and are therefore of great interest primarily as drug‐like molecules. In contrast to the heteroaromatic analogs, synthetic approaches to these compounds were developed much later, and their chemical properties and biological activity have not been studied in detail until recently. In the review, different ways to build dihydroazolopyrimidine systems from different building blocks are described – via the initial formation of a partially hydrogenated pyrimidine ring or an azole ring, as well as a one‐pot assembly of azole and azine fragments. Special attention is given to modern approaches: multicomponent reactions, green chemistry, and the use of non‐classical activation methods. Information on the chemical properties of dihydroazolopyrimidines and the prospects for their use in the design of drugs of various profiles are also summarized in this review.

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“…They can be used as cognitive enhancers for the treatment of neurodegenerative diseases, including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease, Parkinson's disease, AIDS associated dementia, and Down's syndrome, as well as for the treatment of schizophrenia and myoclonus. [24][25][26][27][28] Building upon our earlier investigations, [29][30][31][32][33][34][35][36] this study introduces a new catalyst for the synthesis of polyhydroquinoline and chromene derivatives, specifically the vanadiumoxotetrapyridinoporphyrazine zwitterionic catalyst [VO-(TPPACH 2 CO 2 H)]Cl, which has been modified with acetic acid (Figure 1). This catalyst exhibits dual functionality, possessing both Lewis and Brønsted acid properties within its molecular structure.…”

Section: Introductionmentioning

confidence: 99%

“…Building upon our earlier investigations, [29–36] this study introduces a new catalyst for the synthesis of polyhydroquinoline and chromene derivatives, specifically the vanadium‐oxotetrapyridinoporphyrazine zwitterionic catalyst [VO(TPPACH 2 CO 2 H)]Cl, which has been modified with acetic acid (Figure 1). This catalyst exhibits dual functionality, possessing both Lewis and Brønsted acid properties within its molecular structure.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of a New Zwitterionic Phthalocyanine for Efficient Synthesis of Polyhydroquinoline and Chromene Derivatives

Moeinimehr,

Safaiee,

Taherpour

2024

ChemistrySelect

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This study presents the synthesis and characterization of a new, recyclable, and thermally stable heterogeneous catalyst for the efficient synthesis of polyhydroquinoline and chromene derivatives. The catalyst was characterized using various techniques, including UV spectroscopy, FT‐IR, TGA, DTG, SEM, XRD, ICP Spectroscopy, and CHN analysis. The successfully designed phthalocyanine incorporates both Brønsted and Lewis acid functionality, along with zwitterionic properties. It was effectively utilized in the synthesis of polyhydroquinoline and chromene derivatives. The methodology offers several advantages, such as a simple procedure, excellent yields, and a short reaction time. The findings from this research provide valuable insights into formulating and advancing new catalysts for significant organic reactions.

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Design and synthesis of nickel tetra‐2,3‐pyridiniumporphyrazinato trinitromethanide as an influential catalyst and its application in the synthesis of 1,2,4-triazolo based compounds

Cited by 8 publications

References 38 publications

Synthesis of pyrimidine-6-carbonitriles, pyrimidin-5-ones, and tetrahydroquinoline-3-carbonitriles by new superb oxovanadium(V)-[5,10,15,20-tetrakis(pyridinium)-porphyrinato]-tetra(tricyanomethanide) catalyst via anomeric based oxidation

Synthesis of pyrimidine-6-carbonitriles, pyrimidin-5-ones, and tetrahydroquinoline-3-carbonitriles by new superb oxovanadium(V)-[5,10,15,20-tetrakis(pyridinium)-porphyrinato]-tetra(tricyanomethanide) catalyst via anomeric based oxidation

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Synthesis and Characterization of a New Zwitterionic Phthalocyanine for Efficient Synthesis of Polyhydroquinoline and Chromene Derivatives

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