An Expeditious Oxidative Aromatization of Hantzsch 1,4-Dihydropyridines to Pyridines Using Cetyltrimethylammonium Peroxodisulfate: A Phase Transferring Oxidant

Kumar, Parvin; Kumar, Ashwani

doi:10.5012/bkcs.2010.31.8.2299

Cited by 14 publications

(5 citation statements)

References 55 publications

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“…A yield of 91 % of diethyl 2,6-dimethyl-4phenyl-3,5-pyridinedicarboxylate 15a was obtained. 1 H NMR, IR, and MS data were in accordance with the data previously published (Kumar and Kumar 2010).…”

Section: Synthesis Of Diethyl 26-dimethyl-4-phenyl-35-pyridinedicarboxylatesupporting

confidence: 73%

Lewis acid catalysis and Green oxidations: sequential tandem oxidation processes induced by Mn-hyperaccumulating plants

Escande

Renard

Grison

2014

Environ Sci Pollut Res

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Among the phytotechnologies used for the reclamation of degraded mining sites, phytoextraction aims to diminish the concentration of polluting elements in contaminated soils. However, the biomass resulting from the phytoextraction processes (highly enriched in polluting elements) is too often considered as a problematic waste. The manganese-enriched biomass derived from native Mn-hyperaccumulating plants of New Caledonia was presented here as a valuable source of metallic elements of high interest in chemical catalysis. The preparation of the catalyst Eco-Mn1 and reagent Eco-Mn2 derived from Grevillea exul exul and Grevillea exul rubiginosa was investigated. Their unusual polymetallic compositions allowed to explore new reactivity of low oxidative state of manganese-Mn(II) for Eco-Mn1 and Mn(IV) for Eco-Mn2. Eco-Mn1 was used as a Lewis acid to catalyze the acetalization/elimination of aldehydes into enol ethers with high yields; a new green and stereoselective synthesis of (-)-isopulegol via the carbonyl-ene cyclization of (+)-citronellal was also performed with Eco-Mn1. Eco-Mn2 was used as a mild oxidative reagent and controlled the oxidation of aliphatic alcohols into aldehydes with quantitative yields. Oxidative cleavage was interestingly noticed when Eco-Mn2 was used in the presence of a polyol. Eco-Mn2 allowed direct oxidative iodination of ketones without using iodine, which is strongly discouraged by new environmental legislations. Finally, the combination of the properties in the Eco-Mn catalysts and reagents gave them an unprecedented potential to perform sequential tandem oxidation processes through new green syntheses of p-cymene from (-)-isopulegol and (+)-citronellal; and a new green synthesis of functionalized pyridines by in situ oxidation of 1,4-dihydropyridines.

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Section: Synthesis Of Diethyl 26-dimethyl-4-phenyl-35-pyridinedicarboxylatesupporting

confidence: 73%

Lewis acid catalysis and Green oxidations: sequential tandem oxidation processes induced by Mn-hyperaccumulating plants

Escande

Renard

Grison

2014

Environ Sci Pollut Res

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“…Encouraged by these observation and in continuation of our earlier studies on the oxidative aromatization of 1,4-DHP,s [39][40][41][42] and synthesis of biological active heterocyclic compounds [52][53] , we report herein, solvent free aromatization of diethyl 2, …”

Section: Introductionmentioning

confidence: 55%

Solvent-free synthesis and oxidative aromatization of diethyl-2,6-dimethyl-4-(1-phenyl-3-aryl-1H-pyrazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylates using hypervalent iodine (III) reagents

Kumar¹,

Hussain²,

Kumar³

2014

10.5267/j.ccl

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In this article, an efficient, environmentally benign, solvent-free synthesis of diethyl-2,6-dimethyl-4-(1-phenyl-3-aryl-1H-pyrazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylates and their simple oxidative aromatization in presence of selected hypervalent iodine (III) reagents under solvent-free condition at room temperature is demonstrated. All reactions were carried out by grinding the reactant pyrazole substituted Hantzch-1,4-dihydropyridines and hypervalent iodine (III) reagent in a mortar with pestle. [Hydroxy(tosyloxy)iodo]benzene act as an more efficient oxidizing reagent in comparison to phenyliodine bistrifluoroacetate and iodobenzene diacetate in terms of reaction time and yields. The advantages of present protocol are the environment friendly, short reaction time, mild reaction conditions, and high yields of the products.

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“…It brings advantages from the environmental point of view, as well as rate enhancement, less waste products, and higher yields [32]. In continuation of our previous work [16,[33][34][35][36][37] on biologically active heterocyclic compounds and development of novel synthetic methodologies and because of the biological significance of 1,2,4-triazole, a solvent-free oxidative cyclization of 2-pyridyl-and 2-quinolylhydrazones with phenyliodine bis(trifluoroacetate) (PIFA) or iodobenzene diacetate (IBD) to the corresponding 3-aryl-[1,2,4]triazolo[4,3-a]pyridines and 1-aryl-5-methyl-[1,2,4]triazolo[4,3-a]quinolines is reported here.…”

mentioning

confidence: 79%

An environmentally benign and solvent-free synthesis of 3-aryl[1,2,4]triazolo[4,3-a]pyridines and 1-aryl-5-methyl[1,2,4]triazolo[4,3-a]quinolines using phenyliodine bis(trifluoroacetate) or iodobenzene diacetate

Kumar

2012

Chem Heterocycl Comp

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An Expeditious Oxidative Aromatization of Hantzsch 1,4-Dihydropyridines to Pyridines Using Cetyltrimethylammonium Peroxodisulfate: A Phase Transferring Oxidant

Cited by 14 publications

References 55 publications

Lewis acid catalysis and Green oxidations: sequential tandem oxidation processes induced by Mn-hyperaccumulating plants

Lewis acid catalysis and Green oxidations: sequential tandem oxidation processes induced by Mn-hyperaccumulating plants

Solvent-free synthesis and oxidative aromatization of diethyl-2,6-dimethyl-4-(1-phenyl-3-aryl-1H-pyrazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylates using hypervalent iodine (III) reagents

An environmentally benign and solvent-free synthesis of 3-aryl[1,2,4]triazolo[4,3-a]pyridines and 1-aryl-5-methyl[1,2,4]triazolo[4,3-a]quinolines using phenyliodine bis(trifluoroacetate) or iodobenzene diacetate

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