Benzofuranyl‐pyran‐2‐ones, ‐pyridazines, and ‐pyridones from naturally occurring furochromones (visnagin and khellin)

Keshk, Eman M.

doi:10.1002/hc.10219

Cited by 17 publications

(9 citation statements)

References 20 publications

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“…Keshk synthesized 2 H ‐pyran‐2‐ones ( 343 ) by starting with visnaginone methyl ether ( 339 a ) or khellinone methyl ether ( 339 b ). The corresponding enaminones ( 340 ) were obtained from the acetyl groups with DMF‐DMA, Then, in a reaction vessel, enaminone, N ‐acetylglycine ( 341 ) and acetic anhydride was refluxed for 4 hours, and benzofuran‐5‐yl‐2 H ‐pyran‐2one derivatives ( 343 ) were synthesized in 80–85 % yields [80] . (Scheme 45).…”

Section: Formation Of Heterocycle Structures By Dmf‐dma Reactionsmentioning

confidence: 99%

Enamines and Dimethylamino Imines as Building Blocks in Heterocyclic Synthesis: Reactions of DMF‐DMA Reagent with Different Functional Groups

Gümüş

Koca

2020

ChemistrySelect

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N,N‐Dimethylformamide dimethyl acetal (DMF‐DMA) reagent can react with different functional groups of organic compounds. Enamines and dimethylamino imines are obtained, when the DMF‐DMA reagent is reacted with methylene, methyl and amino groups. These products are formed in the intermediate step in the synthesis of many hetero rings. These compounds are especially used as a starting material in the synthesis of heterostructures such as pyrimidine, pyridine, pyrazole, etc. Therefore, DMF‐DMA has been particularly prominent as a reagent in targeted synthesis and designs of many heterocyclic compounds. Herein, the reactions of DMF‐DMA reagent with different functional groups are categorized in four classes (methylene, methyl, amino, other groups) and the reactions of obtained enamine and dimethylamino imine compounds are investigated in detail such as nucleophilic addition, intramolecular cyclization or condensation reactions. The synthesis and continuation reactions of the enamine and dimethylamino imine compounds are also examined in terms of experimental conditions and reagents used.

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Section: Formation Of Heterocycle Structures By Dmf‐dma Reactionsmentioning

confidence: 99%

Enamines and Dimethylamino Imines as Building Blocks in Heterocyclic Synthesis: Reactions of DMF‐DMA Reagent with Different Functional Groups

Gümüş

Koca

2020

ChemistrySelect

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“…N,N-Dimethylenaminoketones have been used for the synthesis of 2-pyridones using different methylene active compounds (Scheme (42)): cyanoacetamide, cyanoketoesters [155][156][157][158][159] and others, especially thiazole-2-acetamide [160][161]. All require strong basic catalysts such as sodium hydride or alkoxides.…”

Section: From C 3 + C 2 Building Blocksmentioning

confidence: 99%

New Synthetic Methods to 2-Pyridone Rings

Torres¹,

Gil²,

Parra

2005

COC

203

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The synthesis of a substituted 2-pyridone ring is a topical area of continuing interest due to the number of biologically active molecules containing this moiety. Over the last decade, natural compounds with this structure have emerged as potent antitumor antiviral and attention, because those compounds may be studied as a simple model for investigating mechanisms of some enzymatic reactions or for discerning the behavior of nucleic acids bases in connection with mutation due to base mispairing or other mistaken helices. Recent studies have shown the usefulness of 2-pyridones as intermolecular connectors between building blocks in material science. Thus, despite the large number of methods known for their synthesis, new procedures are continuously being developed. Two main synthetic approaches can be found in the literature: from other heterocycles systems or condensation of acyclic systems. The latter can be further classified depending on the bond formed in the cyclization step: by C-C or C-N bond generation. The latter can be subclassified depending on the first condensation step. This is a review of new or improved methods for constructing 2-pyridone rings. This article will be restricted to ring formation, which can be included in the total synthesis of several compounds with specific biological or material properties.The pursuit of these properties requires efficient synthetic routes that allow rapid assembly and variation of multiple pendant substituents on the heteroaromatic case, which permits rapid analogsynthesis (RAS) [1].

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“…In continuation of our research on the synthesis of new heterocyclic compounds derived from the naturally occurring furochromones (visnagin and khellin) of pharmacological interest, 17,18 this work deals with the synthesis and characterization of new compounds containing a benzodifuran nucleus combined with thiosemicarbazide, 1,3,4-triazole, 1,3,4-oxadiazole, thiazolidinone, and 1,3,4-thiadiazole moieties, which are expected to possess high biological activity.…”

Section: Introductionmentioning

confidence: 99%

SYNTHESIS OF BENZO[1,2-b: 5,4-b′]- DIFURANYL-TRIAZOLES, -OXADIAZOLES, -THIAZOLIDINONES, -THIADIAZOLES, AND THE USE OF DNA IN EVALUATION OF THEIR BIOLOGICAL ACTIVITY

Keshk

Abu‐Hashem

Girges

et al. 2004

Phosphorus, Sulfur, and Silicon and the Related Elements

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Benzofuranyl‐pyran‐2‐ones, ‐pyridazines, and ‐pyridones from naturally occurring furochromones (visnagin and khellin)

Cited by 17 publications

References 20 publications

Enamines and Dimethylamino Imines as Building Blocks in Heterocyclic Synthesis: Reactions of DMF‐DMA Reagent with Different Functional Groups

Enamines and Dimethylamino Imines as Building Blocks in Heterocyclic Synthesis: Reactions of DMF‐DMA Reagent with Different Functional Groups

New Synthetic Methods to 2-Pyridone Rings

SYNTHESIS OF BENZO[1,2-b: 5,4-b′]- DIFURANYL-TRIAZOLES, -OXADIAZOLES, -THIAZOLIDINONES, -THIADIAZOLES, AND THE USE OF DNA IN EVALUATION OF THEIR BIOLOGICAL ACTIVITY

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