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1.
Sci Rep ; 12(1): 19537, 2022 11 14.
Article in English | MEDLINE | ID: mdl-36376379

ABSTRACT

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.


Subject(s)
Pyrimidines , Quinolines , Spectroscopy, Fourier Transform Infrared , Catalysis
3.
Mol Divers ; 26(5): 2407-2426, 2022 Oct.
Article in English | MEDLINE | ID: mdl-34694532

ABSTRACT

Three-component reaction of aldehydes with 3-(1H-indol-3-yl)-3-oxopropanenitrile and 1H-1,2,4-triazol-5-amine under the solvent-free condition at 70 °C was effectively performed in the presence of 2 mg of polyionic magnetic nanoparticles with pyrazine bridge [Fe3O4@SiO2@(CH2)3]2-Pyrazinium-[TCM]2 as a catalyst for the synthesis of 7-aryl-5-(1H-indol-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles via a cooperative anomeric-based oxidation. The polyionic magnetic nanoparticles catalyst was simply recovered and reused four successive runs. The morphology and structure of MNPs catalyst were investigated by numerous techniques such as XRD, FT-IR, EDX, WDX, FE-SEM, TEM, TGA, DTA, and VSM. The obtained products are reported for the first time that were identified by various analyses techniques such as melting point, FT-IR, 1H NMR, 13C NMR, and elemental analysis (CHN). A term entitled a cooperative geminal-vinylogous anomeric-based oxidation was introduced for the latter step of the reaction mechanism for the first time. Synthesis of 7-aryl-5-(1H-indol-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles by using [Fe3O4@SiO2@(CH2)3]2-Pyrazinium-[TCM]2 MNPs as a catalyst.


Subject(s)
Magnetite Nanoparticles , Triazoles , Aldehydes , Amines , Indoles/chemistry , Magnetite Nanoparticles/chemistry , Pyrazines , Pyrimidines , Silicon Dioxide/chemistry , Spectroscopy, Fourier Transform Infrared
4.
RSC Adv ; 10(46): 27824-27834, 2020 Jul 21.
Article in English | MEDLINE | ID: mdl-35516925

ABSTRACT

Cobalt tetra-2,3-pyridiniumporphyrazinato with sulfonic acid tag [Co(TPPASO3H)]Cl was produced and catalyzed the synthesis of ortho-aminocarbonitriles, cyclohexa-1,3-dienamines and 2-amino-3-cyanopyridines. The synthesis of 2-amino-3-cyanopyridines by using [Co(TPPASO3H)]Cl proceeded via a cooperative vinylogous anomeric based oxidation mechanism. [Co(TPPASO3H)]Cl can be recycled and reused six times with a marginal decreasing of its catalytic activity.

5.
Comb Chem High Throughput Screen ; 16(8): 618-27, 2013 Sep.
Article in English | MEDLINE | ID: mdl-23547570

ABSTRACT

In this paper, we introduce two nonconventional ionic liquid compounds which are composed of propane sulfonate functionalized organic cations and heteropolyanions as green solid acid catalysts for the highly efficient and green synthesis of 2,3-disubstitutedquinoxaline derivatives. These ionic liquids are in the solid state at room temperature and the synthesis is carried out via the one-pot condensation reaction of various o-phenylenediamine with 1,2-diketone derivatives. Benzoxazole and benzimidazole derivatives were also synthesized by these novel catalysts via the one-pot condensation from reaction orthoester with o-aminophenol (synthesis of benzoxazole derivatives) and ophenylenediamine (synthesis of benzimidazole derivatives). All experiments successfully resulted in the desired products. The described novel synthesis method has several advantages of safety, mild condition, high yields, short reaction times, simplicity and easy workup compared to the traditional method of synthesis.


Subject(s)
Benzimidazoles/chemical synthesis , Benzoxazoles/chemical synthesis , Ionic Liquids/chemistry , Quinoxalines/chemical synthesis , Catalysis , Green Chemistry Technology
6.
Comb Chem High Throughput Screen ; 16(1): 2-6, 2013 Jan.
Article in English | MEDLINE | ID: mdl-22998593

ABSTRACT

The catalytic property of Cu(II) Schiff-base complex in an efficient synthesis of 1,8-dioxodecahydroacridines was investigated. The one-pot three component reaction of dimedone, aromatic aldehydes and aromatic amines or ammonium acetate in water afforded the corresponding 1,8-dioxodecahydroacridines with excellent yields. This reaction was carried out in the presence of 1 mol% of catalysts at room temperature. The reusability of the catalysts was demonstrated by a five-run test without loss of its activity. Also, this catalyst possesses several advantages including mild reaction conditions, lower catalytic loading, shorter reaction times, high yield of the products, inexpensive and cleaner (Green chemistry) reactions.


Subject(s)
Acridines/chemical synthesis , Coordination Complexes/chemistry , Copper/chemistry , Schiff Bases/chemistry , Acridines/chemistry , Catalysis , Combinatorial Chemistry Techniques , Green Chemistry Technology
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