Homologues of pyridine. II. Synthesis and reactions of some α,α'-disubstituted pyridines

Lukeš, R.; Pergal, Marija V.

doi:10.1135/cccc19590036

Cited by 18 publications

(9 citation statements)

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“…Similarly, 2,6-diacetylpyridine dioxime 2 and 2,6-bis-[β -(2-thienyl)acryloyl]pyridine 3 were prepared as starting materials according to literature reports [4,17]. Condensation of compound 3 with hydroxylamine hydrochloride in pyridine afforded the corresponding 2,6-bis[β -(thienyl)acryloyl]pyridine dioxime 6 (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of Some New Linear and Chiral Macrocyclic Pyridine Carbazides as Analgesic and Anticonvulsant Agents

Amr

2005

Zeitschrift Für Naturforschung B

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A series of 2,6-disubstituted pyridine derivatives were prepared from 2,6-diacetylpyridine or 2,6-dicarbonyl pyridine dichloride as starting materials. Reaction of 2,6-diacetylpyridine 1 with hydroxylamine hydrochloride or different aromatic aldehydes afforded the corresponding 2,6-diacetylpyridine dioxime and 2,6-bis-[β -(2-thienyl)acryloyl]pyridine derivatives 2 and 3, respectively. Additionally, N 2 , N 2' -(pyridine-2,6-dicarbonyl)-L-amino acid hydrazides 5 were prepared starting from 2,6-dicarbonyl pyridine dichloride via the corresponding esters 4. Compound 3 was reacted with hydroxylamine hydrochloride to afford the 2,6-bis-[β -(2-thienyl)acryloyl-oxime]-pyridine derivative 6. Treatment of compounds 2 or 6 with phenyl isocyanate or phenyl isothiocyanate in refluxing dioxane gave the corresponding semicarbazide or thiosemicarbazide derivatives 7 and 8, respectively. Their treatment with toluene-3,5-diisocyanate afforded the macrocyclic semicarbzides 9 and 10, respectively. The chiral thiosemicarbazides 11a,b were however, prepared by treating compounds 5a,b with phenyl isothiocyanate followed by cyclization with sodium hydroxide (2N) yielding the triazoles 12a,b. Finally, the hydrazides 5a,b were treated with toluene-3,5-diisocyanate to afford the chiral macrocyclic tetrapeptide semicarbazides 13a,b in reasonable yields, while the expected cyclic dipeptide 14 was not formed. The structure assignments of the new compounds were based on chemical and spectroscopic evidence.The pharmacological screening showed that many of these compounds have good analgesic and anticonvulsant activities comparable to Voltarine R and Carbamazapine R used as reference drugs.

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Section: Resultsmentioning

confidence: 99%

“…All reactions were followed by TLC (Silica gel, aluminum sheets 60F 254 , Merck). The starting materials 2, 3 and 5 were prepared according to the reported procedures [1,2,4,5,17].…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Some New Linear and Chiral Macrocyclic Pyridine Carbazides as Analgesic and Anticonvulsant Agents

Amr

2005

Zeitschrift Für Naturforschung B

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“…2,6-Diacetylpyridine (DAP) was prepared from the former reagent via 2,6-dimethylpyridinedicarboxylate 28 as described by Lukes and Pergál. 36 2,6-Diformylpyridine (DFP) was prepared in one step from 2,6-pyridinedimethanol by a SeO 2 oxidation. 37 2,6-Diformyl-4-methylphenol was prepared according to the literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Tricopper(ii) complexes of unsymmetrical macrocycles incorporating phenol and pyridine moieties: the development of two stepwise routes

et al. 2007

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Two stepwise approaches to preparing large unsymmetrical macrocycles incorporating diethylenetriamine lateral units are described: the first utilises protecting group chemistry, whereas the second exploits irreversible amide bond formation in the presence of an excess of the amine. In the first approach condensation of two equivalents of N-acetyldiethylenetriamine 1 with 2,6-diformyl-4-methylphenol, followed by a sodium borohydride reduction of the newly formed imine bonds and acidic removal of the protecting groups, yields a phenol-containing "two-armed" precursor as an HCl salt 2. Using the second approach the new pyridine-containing "two-armed" precursor , is prepared from 2,6-dimethylpyridinedicarboxylate and an excess of diethylenetriamine. These two "two-armed" di-primary amine precursors, 2 (after reaction with KOH) and 3, can be condensed with the dicarbonyl head units of choice. The lead templated condensation of 2 with 2,6-diacetylpyridine results in the formation of the macrocyclic dilead(II) complex {[Pb(II)(2)(L1)(Cl)](ClO(4))(2)}(infinity) 4. Transmetallation of 4 with three equivalents of copper(II) perchlorate produces Cu(II)(3)(L1)(OH)(ClO(4))(4) 5. Condensation of 3 with 2,6-diacetylpyridine or 2,6-diformylpyridine in the presence of barium(ii) ions results in the macrocyclic complexes [Ba(II)(H(2)L2)](ClO(4))(2) 6 and [Ba(II)(H(2)L3)](ClO(4))(2) 7, respectively. Copper(II) acetate templates the formation of the crystallographically characterised unsymmetrical macrocyclic complex [Cu(II)(3)(L4)(OH)(NCS)(2)].EtOH, 8.EtOH, from 3, 2,6-diformyl-4-methylphenol and NaNCS.

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“…Experimental Material 2,6-diacetylpyridine(dap), 3-oxapentane-l,5-diamine(opa) was synthesized according to the literature. 16 Nitrotetrazolium blue (NBT), Emethionine, and riboflavin are of B.R. grade.…”

Section: Introductionmentioning

confidence: 99%

A study on some macrocyclic bicopper(II) complexes as the model compounds of superoxide dismutase

1996

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ZCMembered macrocyclic bicopper(I1) complexes wth bridging ligand imidzae late, SCN-, N; and H2O respectively were synthesized by condensation of diacetylpyridine with 3-oxapentane-1,5-diamine. As the model compounds of superoxide dismutase (SOD), the relationship between their SOD activities and properties of bridging ligands and redox potentials of copper(I1) were studied. Macrocyclic bicopper(I1) complexes 115 5 (0.2174 g, 0.2 mmol), acetonitrile solution (20 mL) containing Cu(C104)2.6H20

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Homologues of pyridine. II. Synthesis and reactions of some α,α'-disubstituted pyridines

Cited by 18 publications

References 1 publication

Synthesis of Some New Linear and Chiral Macrocyclic Pyridine Carbazides as Analgesic and Anticonvulsant Agents

Synthesis of Some New Linear and Chiral Macrocyclic Pyridine Carbazides as Analgesic and Anticonvulsant Agents

Tricopper(ii) complexes of unsymmetrical macrocycles incorporating phenol and pyridine moieties: the development of two stepwise routes

A study on some macrocyclic bicopper(II) complexes as the model compounds of superoxide dismutase

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