Synthesis and characterization of 2,6-bis-hydrazinopyridine, and its conversion to 2,6-bis-pyrazolylpyridines

Brien, Kimberly A.; Garner, Charles M.; Pinney, Kevin G.

doi:10.1016/j.tet.2006.01.086

Cited by 22 publications

(17 citation statements)

References 14 publications

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“…Condensation of 3a,b with 1,3-dicarbonyl compounds gave the respective pyrazole and pyrazolidinone derivatives. Thus, reaction of 3a,b with acetylacetone in dioxane gave 2-(3,5-dimethylpyrazol-1-yl)-5-N-arylaminomethyl-1,3,4-oxadiazoles 11a,b, via a known mechanism [32] that involved initial reaction of the NH 2 group of 3a,b with one carbonyl group of the diketone, followed by cyclization of the remaining carbonyl to form the pyrazole ring (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antiviral Evaluation of Novel 5‐(N‐Aryl‐aminomethyl‐1,3,4‐oxadiazol‐2‐yl)hydrazines and Their Sugars, 1,2,4‐Triazoles, Tetrazoles and Pyrazolyl Derivatives

Abdel‐Aal

El-Sayed

El-Kosy

et al. 2008

Archiv der Pharmazie

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A number of new N-arylaminomethyl-1,3,4-oxadiazole derivatives 2, 3a,b, and 9-12a,b were prepared. Sugar (5-N-arylaminomethyl-1,3,4-oxadiazol-2-yl) hydrazones 4-6a,b were synthesized by the reaction of the hydrazino derivatives 3a,b with the corresponding monosaccharides. The novel acyclo-C-nucleosides 7, 8a,b were prepared by heterocyclization of the sugar hydrazones 4, 5a,b with acetic anhydride. A number of the synthesized compounds were tested for their antiviral activity against herpes simplex virus type-1 (HSV-1) and hepatitis-A virus (HAV, MBBcell culture-adapted strain). The results revealed that the sugar hydrazones 6a,b showed higher antiviral activity compared to the other hydrazones and their acetylated derivatives.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Antiviral Evaluation of Novel 5‐(N‐Aryl‐aminomethyl‐1,3,4‐oxadiazol‐2‐yl)hydrazines and Their Sugars, 1,2,4‐Triazoles, Tetrazoles and Pyrazolyl Derivatives

Abdel‐Aal

El-Sayed

El-Kosy

et al. 2008

Archiv der Pharmazie

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“…28 4',4''-Dinitro-1-bppyz was prepared by eq 1, however, starting from preformed 4-nitropyrazole. 22 4',4''-Dinitro-1-bpp cannot be made 75 by that route, because the more forcing conditions required leads to decomposition of the nitropyrazole reagents. is the most common route for attaching additional functionality to the 1-bpp pyridine ring.…”

Section: Synthesis Of 1-bpp Derivatives and Related Ligandsmentioning

confidence: 99%

Recent advances in the synthesis and applications of 2,6-dipyrazolylpyridine derivatives and their complexes

Halcrow

2014

New J. Chem.

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Developments in the chemistry of 2,6-di(pyrazol-1-yl)pyridine (1-bpp) and 2,6-di(pyrazol-3-yl)pyridine (3-bpp), their derivatives and their complexes are surveyed, with emphasis on the last eight years. Particular advances include the synthesis of multi-functional spin-crossover switches; the incorporation of emissive f-element podand centres into biomedical sensors; the self-assembly of a variety of functional soft materials and surface structures; and, the use of 3-bpp complexes in catalysis.

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“…Hydrazine-substituted heterocyclic ligands are useful for preparation of a wide variety of pyrazolyl derivatives [9]. Free macrocycles incorporating bpy or phen have been synthesized by template condensation of 6,6 0 -bis(hydrazino)-2,2 0 -bipyridine or 2.9-bis(hydrazino)-1,10-phenanthroline with dicarbonyl ligands in the presence of Cr(III) [10] and also by cyclization of the corresponding hydrazino complexes of Ni(II) or Co(II) with aqueous acetone and other -methyl ketones or aldehydes [11,12].…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic and structural studies of 6,6′-bis(N-methylhydrazine)-2,2′-bipyridine and its mononuclear copper(II) complex

Şengül

Yılmaz

Şahin

et al. 2010

Journal of Coordination Chemistry

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The tetradentate ligand, 6,6 0 -bis(N-methylhydrazine)-2,2 0 -bipyridine (L) and its mononuclear copper(II) complex [Cu(L)](ClO 4 ) 2 ] (1) have been synthesized and characterized. The crystal structures of L and 1 have been determined by single-crystal X-ray diffraction. Both crystallize in the centrosymmetric monoclinic space group with crystallographic inversion symmetry. The ligand adopts a planar transoid configuration in the solid state. In 1, the Cu(II) is six-coordinate octahedral, defined by N 4 O 2 donors from ligand and two perchlorates. The molecular units are connected by intermolecular H-bonds between the hydrazino group of the one unit and coordinated perchlorate of the neighboring two units via N-H Á Á Á O to furnish a 2-D network. Coordinated perchlorates also form an intramolecular H-bond with hydrazine influencing the crystal packing.

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Synthesis and characterization of 2,6-bis-hydrazinopyridine, and its conversion to 2,6-bis-pyrazolylpyridines

Cited by 22 publications

References 14 publications

Synthesis and Antiviral Evaluation of Novel 5‐(N‐Aryl‐aminomethyl‐1,3,4‐oxadiazol‐2‐yl)hydrazines and Their Sugars, 1,2,4‐Triazoles, Tetrazoles and Pyrazolyl Derivatives

Synthesis and Antiviral Evaluation of Novel 5‐(N‐Aryl‐aminomethyl‐1,3,4‐oxadiazol‐2‐yl)hydrazines and Their Sugars, 1,2,4‐Triazoles, Tetrazoles and Pyrazolyl Derivatives

Recent advances in the synthesis and applications of 2,6-dipyrazolylpyridine derivatives and their complexes

Spectroscopic and structural studies of 6,6′-bis(N-methylhydrazine)-2,2′-bipyridine and its mononuclear copper(II) complex

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