Reaction of 3-Arylmethylidene-3H-furan-2-ones with 3-Amino-1,2,4-triazole as a Convenient Technique to Synthesize Condensed Diazepinones

Anis’kova, T. V.; Chadina, V. V.; Egorova, A. Yu.

doi:10.1080/00397911.2010.502989

Cited by 13 publications

(4 citation statements)

References 5 publications

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“…10,11 5-R-3-arylmethylidene-3H-furan-2-ones may be used as accessible and promising substrates in 1,3-dipolar cycloaddition reactions. 12,13 Previously, these little studied compounds have been introduced in cycloaddition reaction with azomethine imines, generated in situ from hydrazones. 14 Based on these substrates the assembly of dispirocyclic systems containing the oxoindole moiety is possible in one step if suitable 1,3-dipoles are employed.…”

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confidence: 99%

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Reaction of arylmethylidene derivatives of 3H-furan-2-ones with azomethine ylide

Anis’kov

Kamneva

Zheleznova

et al. 2015

Chem Heterocycl Comp

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confidence: 99%

“…The process was found to proceed diastereoselectively as an endo cycloaddition to form previously unknown dispiropyrrolidines. 13 С, HSQC 1 Н-13 С, ASAPHMQC 1 Н-13 С, 1D and 2D NOESY NMR spectra were registered on a Varian 400 (400 and 100 MHz for 1 Н and 13 С nuclei, respectively) spectrometer. Solvents: CD 3 COCD 3 (compounds 2b,d) and …”

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confidence: 99%

Reaction of arylmethylidene derivatives of 3H-furan-2-ones with azomethine ylide

Anis’kov

Kamneva

Zheleznova

et al. 2015

Chem Heterocycl Comp

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“…Arylmethylidene derivatives are also available as scaffolds for the synthesis of various heterocyclic compounds of different complexity. These substances combine the properties of unsaturated carbonyl compounds and esters, allowing the implementation of reactions with various C-nucleophiles such as acetoacetic ester [ 18 ], acetylacetone [ 19 ], cyclohexanone [ 20 ], and mono- and N , N -binucleophiles [ 21 , 22 ]. Owing to the presence of a conjugated double bond, arylidene derivatives can easily add azides [ 23 , 24 ] oxygen (to give rise corresponding epoxides [ 25 ]), and halogen [ 26 ].…”

Section: Introductionmentioning

confidence: 99%

Structure, Z′ = 2 Crystal Packing Features of 3-(2-Chlorobenzylidene)-5-(p-tolyl)furan-2(3H)-one

et al. 2021

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3-(2-Chlorobenzylidene)-5-(p-tolyl)furan-2(3H)-one (1), C18H13ClO2, crystallizes with Z = 8 and Z′ = 2, and the structure at 100 K has orthorhombic (Pna21) symmetry. Each kind of molecule takes part in π–π stacking interactions to form infinite chains parallel to the c axis. We believe that the existence of two forms can be explained by the probable rotation around a single C–C bond. The quantum chemical modeling reveals that these molecules are almost equivalent energetically, and they can be described as the two most stable conformers (rotamers) with a minor rotational barrier of about 0.67 kcal/mol.

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“…As a substrate, 3-arylmethylidenefuran-2(3 H )-ones have some advantages. They can be easily obtained, and they are convenient, cost-effective substrates for the synthesis of various hard-to-reach heterocyclic, spirocyclic, and polycyclic compounds [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 ]. 3-Arylmethylidenefuran-2(3 H )-ones are substances which combine the properties of internal esters and α,β-unsaturated carbonyl compounds, and they are able to react with substances with mobile hydrogen atoms.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Compounds of the Pyrimidine Series Based on the Reactions of 3-Arylmethylidenefuran-2(3H)-ones with N,N-Binucleophilic Reagents

2017

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The arylmethylidene derivatives of furan-2(3H)-ones are important building blocks for the synthesis of various heterocyclic compounds containing pyrimidine and pyridazine structural fragments, analogues of nitrogen-containing bases of pyrimidine series. In order to continue the development of constructing of molecules containing pyridine and pyridazine fragments, this article is devoted to the synthesis of new biologically active compounds with these moieties. The introduction of a heterocyclic chromenone fragment changes the previously observed 5-R-3-arylmethylidenefuran-2(3H)-ones route of reaction with guanidine carbonate and leads to 3-[(2-amino-4-(2-hydroxyphenyl)pyrimidin-5-yl)methylene]-5-phenylfuran-2(3H)-ones (2a–d). The structure of the reaction products depends on the nature of the aromatic substituent at the C-3 position of the furanone ring. The interaction of 5-aryl-3-arylmethylidenefuran-2(3H)-ones (1e–h) with thiourea in the basic medium leads to the isolation of 5-(2-oxo-2-phenylethyl)-6-aryl-2-thioxotetrahydropyrimidine-4(1H)-ones (3a–d), demonstrating pronounced plant-growth regulatory activity. Optimal conditions for all discussed processes were developed.

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Reaction of 3-Arylmethylidene-3H-furan-2-ones with 3-Amino-1,2,4-triazole as a Convenient Technique to Synthesize Condensed Diazepinones

Cited by 13 publications

References 5 publications

Reaction of arylmethylidene derivatives of 3H-furan-2-ones with azomethine ylide

Reaction of arylmethylidene derivatives of 3H-furan-2-ones with azomethine ylide

Structure, Z′ = 2 Crystal Packing Features of 3-(2-Chlorobenzylidene)-5-(p-tolyl)furan-2(3H)-one

Synthesis of Compounds of the Pyrimidine Series Based on the Reactions of 3-Arylmethylidenefuran-2(3H)-ones with N,N-Binucleophilic Reagents

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