Synthesis, antifungal activity and semi-empirical AM1-MO calculations of some new 4-oxo-4H-chromene derivatives

El‐Shaaer, Hafez M.; Abdel‐Aziz, Salah A.; Ali, Tarik E.; El-Fauomy, A. Z.

doi:10.5155/eurjchem.2.2.158-162.381

Cited by 8 publications

(11 citation statements)

References 20 publications

(14 reference statements)

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“…In our recent work, we described the reaction of 4‐oxo‐4 H ‐1‐benzopyran‐3‐carboxaldehyde derivatives with aminobenzothiazoles , hydrazides , hydrazinecarbodithioic acid , p ‐phenylenediamine , N ‐aminobicyclo[2.2.1]‐5‐heptene‐2,3‐dicarboximide , and 4‐amino‐6‐methyl‐ 3‐thioxo‐1,2,4‐triazin‐5(2 H )one in different reaction conditions.…”

Section: Resultsmentioning

confidence: 99%

Study of the Reactivity of 6,8‐Dimethyl‐4‐oxo‐4H‐1‐benzopyran‐3‐carboxaldehyde Towards Amino‐6‐oxopyridine‐3‐carboxylate Derivatives

El‐Shaaer

Abdel-Monem

Ibrahim

et al. 2014

Journal of Heterocyclic Chem

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The condensation reactions of 6,8‐dimethyl‐4‐oxo‐4H‐1‐benzopyran‐3‐carboxaldehyde (1) with equimolar amounts of ethyl 2‐amino‐4‐(4‐chlorophenyl)‐5‐cyano‐1‐[(5,6‐diphenyl‐1,2,4‐triazin‐3‐yl)amino]‐6‐oxo‐1,6‐dihydropyridine‐3‐carboxylate (2) at different reaction conditions gave different chromanone and chromenone products 3, 4, 5. Also, the condensation reactions of compound 1 with ethyl 5‐cyano‐1,2‐diamino‐4‐(3‐nitrophenyl)‐6‐oxo‐1,6‐dihydropyridine‐3‐carboxylate (6) in absolute ethanol, dry benzene, acetic acid, and/or dry xylene gave a variety of products 7, 8, 9, 10 depending on the solvent used.

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Section: Resultsmentioning

confidence: 99%

Study of the Reactivity of 6,8‐Dimethyl‐4‐oxo‐4H‐1‐benzopyran‐3‐carboxaldehyde Towards Amino‐6‐oxopyridine‐3‐carboxylate Derivatives

El‐Shaaer

Abdel-Monem

Ibrahim

et al. 2014

Journal of Heterocyclic Chem

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“…Chemoselective reduction of imine group was found though there is a possibility of reduction of double bond at C 2 position of 21 . Compound 23 reacted with 1 under similar conditions and gave 24 in 30–35% yield through condensation followed by 1,4‐addition with the solvent molecules (Scheme ).…”

Section: Reaction With Nitrogenous Nuclophilesmentioning

confidence: 99%

Synthesis and Chemical Reactivity of 4‐Oxo‐4H‐1‐benzopyran‐3‐carboxaldehyde

Sepay

Dey²

2014

Journal of Heterocyclic Chem

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4‐Oxo‐4H‐1‐benzopyran‐3‐carboxaldehyde (chromone‐3‐carboxaldehyde or 3‐formylchromone) 1 is an important biologically active compound. It can serve as a precursor in the synthesis of a wide range of heterocyclic systems having chromone moiety, many of which exhibit broad spectrum of biological activities such as anti‐mutagenisity, cytotoxicity, thymidine phosphorylase inhibitor, and anti‐HIV activity. During the last decade, the title compound was studied extensively. The review presents an overall survey of the synthesis, chemical reactivity, and biological activities of 4‐oxo‐4H‐1‐benzopyran‐3‐carboxaldehydes and some of its derivatives.

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“…A large group of 3-(aryl/heteroaryliminomethyl)chromone derivatives 156 were prepared from condensation reactions of 3-formylchromones 1a-d with a variety of aryl/hetarylaminesin non polar solvents such as benzene, toluene or xylene under reflux, in the presence of p-toluenesulfonic acid as a catalyst (Scheme 76) [100][101][102][103][104][105][106][107][108].…”

Section: Reactions With Primary Aminesmentioning

confidence: 99%

“…On the other hand, reaction of 3-formylchromones 1a-c with equimolar ratio of aryl/hetarylamines 157 in boiling ethanol gave 3-(aryl/hetarylaminomethylene)-2-(ethoxy) chromones 158, but when the reaction took place with two moles of 157 in dry toluene, the 1,4-adducts 159 were obtained (Scheme 77) [105][106][107][108][109][110][111][112][113][114][115].…”

Section: Scheme 76mentioning

confidence: 99%