Synthesis, molecular, electronic structure, linear and non-linear optical and phototransient properties of 8-methyl-1,2-dihydro-4H-chromeno[2,3-b]quinoline-4,6(3H)-dione (MDCQD): Experimental and DFT investigations

Al‐Harbi

Allehyani

2020

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The chemical behavior of 4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromene-6-carbonitrile (1) was investigated toward some acyclic and cyclic active methylene ketones namely acetylacetone, ethyl acetoacetate, ethyl benzoylacetate, acetoacetanilide, dimedone, indanedione, pyrazolidine-3,5-dione and 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, barbituric acid and 1-allylthiobarbituric acid, and hippuric acid. A variety of novel heteroannulated furochromenopyridines were efficiently synthesized through a cascade reactions between 4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromene-6-carbonitrile (1) and the carbon nucleophilic reagents. Structures of the new products were inferred based on their analytical and spectral data.

Section: Resultsmentioning

confidence: 99%

Synthesis and antimicrobial evaluation of the novel heteroannulated furo[3′,2′:6,7]chromeno[2,3‐b]pyridines: Part 1

Al‐Harbi

Allehyani

2020

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“…Chromone derivatives shown diverse biological activities including antitumor, 1,2 anticancer, 3,4 antimicrobial, 5 antioxidant, 6,7 antiinflammatory, 8 neuroprotective, 9 and HIV‐inhibitory 10 . Electronic absorption spectra, quantum chemical studies, DFT calculations, and optical properties were investigated for chromone derivatives 10–13 . Recently, enaminone derivatives represent a good source for synthesis of a diversity of 3‐substituted chromones 14–16 .…”

Section: Introductionmentioning

confidence: 99%

Reactivity of some 3‐substituted‐6,8‐dimethylchromones toward some nucleophilic reagents

Badran

El‐Gohary

et al. 2020

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The reactivity of 3‐substituted‐6,8‐dimethylchromone derivatives 1‐5 was investigated toward selected nucleophilic reagents namely; 3‐amino‐1,2,4‐triazole, 2‐aminobenzimidazole, 7‐chloro‐4‐hydrazinoquinoline, and 5,6‐diphenyl‐3‐hydrazino‐1,2,4‐triazine. These nucleophiles were allowed to react with 6,8‐dimethylchromone‐3‐carboxaldehyde (1) through condensation with the aldehyde group with opening of γ‐pyrone ring giving compounds 6, 7, 10, and 11. Reactions with 6,8‐dimethylchromone‐3‐carbonitrile (2), and 6,8‐dimethylchromone‐3‐carboxylic acid (3) occur via attack at position 2 in both compounds followed by cycloaddition onto the nitrile function (in case of carbonitrile 2) or decarboxylation and cyclocondensation with the carbonyl group (in case of carboxylic acid 3). The current nucleophilic reagents reacted with simple condensation products 4 and 5, in boiling dioxane, through nucleophilic addition at the exocyclic vinyl bond followed by addition at the CN group giving 6,8‐dimethylchromone linked various heterocyclic systems 20‐27.

“…Chromones displayed various biological applications including anticancer , anti‐HIV , neuroprotective , antioxidant , anti‐inflammatory , antibacterial , antibiotic , antimalarial agents , α‐glucosidase and acetylcholinesterase inhibitors , and treatment of Alzheimer's disease . Recently, chromone derivatives were used in a range of optoelectronic applications . Chromones bearing an electron‐withdrawing groups at position 3 revealed a variety of transformations upon treatment with nucleophilic reagents .…”

Section: Introductionmentioning

confidence: 99%

Ring Opening and Recyclization Reactions with Chromone‐3‐carbonitrile

El-Kazak

2019

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Chemical transformations of chromone‐3‐carbonitrile (1) with some substituted hydrazines, namely, thiosemicarbazide, S‐methyl/benzyldithiocarbazate, 7‐chloro‐4‐hydrazinoquinoline, and 3‐hydrazino‐5,6‐diphenyl‐1,2,4‐triazine, led to substituted pyrazoles 2, 5–8. Ring opening of carbonitrile 1 followed by recyclization with 3‐amino‐1,2,4‐triazole and 2‐aminobenzimidazole gave triazolo[1,5‐a]pyrimidine 9 and pyrimido[1,2‐a]benzimidazole 10, respectively. Treatment of carbonitrile 1 with some heterocyclic amines produced 2‐amino‐3‐substituted‐chromones 11 and 12. The novel 3‐hydroxychromeno[4,3‐b]pyrazolo[4,3‐e]pyridin‐5(1H)‐one (13) was efficiently synthesized from the ring conversion of carbonitrile 1 with cyanoacetohydrazide. A mixture of chromeno[2,3‐b]naphthyridine 14 and chromeno[4,3‐b]pyridine 15 was obtained from base catalyzed transformation of carbonitrile 1 with malononitrile dimer. A diversity of novel annulated chromeno[2,3‐b]pyridines 16–22 was also synthesized. Chromeno[2,3‐b]pyrrole‐2‐carboxylate 23 was obtained from the reaction of carbonitrile 1 with ethyl chloroacetate. Structures of the new synthesized products were deduced on the basis of their analytical and spectral data.