N-(2-Vinyloxyethyl)-4,5-dihydro-1H-pyrazoles

Kukharev, B. F.; Stankevich, V. K.; Lobanova, N. A.; Klimenko, G. R.; Sadykov, E. Kh.

doi:10.1134/s1070428007040264

Cited by 4 publications

(3 citation statements)

References 1 publication

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“…White solid (480 mg, 68%); mp 114-116 °C; 1 H NMR (400 MHz, CDCl 3 ): δ 2.98 (t, 2H, 3 J = 5.2 Hz, 1″-CH 2 ), 3.77 (t, 2H, 3 J = 5.2 Hz, 2″-CH 2 ), 3.85 (s, 3H, 4′-OCH 3 ), 4.23 (s, 2H, 10-CH 2 ), 5.00 (s, 2H, 8-CH 2 ), 6.89 (d, 1H, 3 J = 8.9 Hz, 6-H), 6.98 (d, 2H, 3 J = 9 Hz, 3′, 5′-H), 7.49 (d, 2H, 3 J = 9 Hz, 2′, 6′-H), 7.93 (s, 1H, 2-H), 8.10 ppm (d, 1H, 3 J = 8.9 Hz, 5-H); 13 Method B. A solution of 2.5 mmol of isoflavone 3a or 3d, 3 mmol of bis(1,3-oxazolidin-3-yl)methane 55,56 in 10 mL of 1,4dioxane was refluxed for 2-4 h. The mixture was cooled; the solvent was evaporated; and the product was treated with hexane to obtain a precipitate that was recrystallized from a mixture of isopropanol and hexane to afford 3a or 3d. Compounds 3a and 3d were identical to material synthesized by Method A.…”

Section: General Procedures For the Aminomethylation Of 7-hydroxyisof...mentioning

confidence: 99%

Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals

et al. 2015

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The aminomethylation of hydroxylated isoflavones with 2-aminoethanol, 3-amino-1-propanol, 4-amino-1-butanol, and 5-amino-1-pentanol in the presence of excess formaldehyde led principally to 9-(2-hydroalkyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]-oxazin-4-ones 4 and/or the tautomeric 7-hydroxy-8-(1,3-oxazepan-3-ylmethyl)-4H-chromen-4-ones 5. The ratio of these tautomers was dependent on solvent polarity, electronic effects of aryl substituents in the isoflavone and the structure of the amino alcohol. NMR studies confirmed the interconversion of tautomeric forms.

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Section: General Procedures For the Aminomethylation Of 7-hydroxyisof...mentioning

confidence: 99%

Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals

et al. 2015

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“…Polymer Chemistry linked to the N of the pyrazoline ring system is reactive and readily substituted to produce pyrazoline derivatives. 31 The different residue groups are generated from the high reaction temperature and different catalysts.…”

Section: Papermentioning

confidence: 99%

Synthesis and characterization of fluorescent oligo(3,4,5-triethoxycarbonyl-2-pyrazoline)

Jia

Xiao

et al. 2014

Polym. Chem.

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Pseudopeptide oligomers as newly developing fluorescent macromolecules are of significant importance and fairly attractive in bioimaging of living cells. We report that a type of efficient fluorescent pseudopeptide oligo(3,4,5-triethoxycarbonyl-2-pyrazoline) is prepared by the novel cyclopolycondensation of 3,4,5-triethoxycarbonyl-2-pyrazoline that is a weakly-fluorescent chromophore.The pseudopeptide oligomer exhibits a strong red-shift and remarkable fluorescence enhancement compared with the monomer 2-pyrazoline and images living cells in good quality, even though it only consists of fewer than 70 glycine residues whereas for the famous green fluorescent protein (GFP) the amount of the various natural amino acid residues is 238. Oligo(3,4,5-triethoxycarbonyl-2-pyrazoline) is a GFP-mimetic but structurally-simplified fluorescent pseudopeptide with simple chemistry, generated from the only natural resource of glycine.

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“…13,14 In particular, the 1,3-dipolar cycloaddition gives rise to the five-membered heterocyclic pyrazoline. This 2-pyrazoline ring system is a valuable and intriguing scaffold that is widely utilized in organic synthesis for other kinds of compounds via further transformation 15,16 and is also the core structure of numerous molecules in the application of fluorescent sensors, 17 fluorescent dyes 18 and pharmacology. 19 2-Pyrazoline usually appears as a ubiquitous compound in the reaction of α-diazoacetates, 20 and meanwhile lots of asymmetric pyrazolines are synthesized under mild conditions, 21,22 proving that the 1,3-dipolar cycloaddition can occur easily.…”

Section: Introductionmentioning

confidence: 99%

One-pot catalyst-free synthesis of down- and upconversion fluorescent oligopyrazolines from diazoacetates and maleic anhydride

Jia

et al. 2015

Polym. Chem.

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Conventionally, each fluorophore is only illuminated with the wavelength of incident light shorter (downconversion) or longer (upconversion) than that of emitted light. However, the oligopyrazolines presented in this paper are the down-and upconversion fluorescent molecules with a maximum emission at 445 nm, which are facilely synthesized from diazoacetates and maleic anhydride (MA) without any catalyst by a newly developed one-pot process. The intermediates of oligopyrazolines are formed through 1,3dipolar cycloaddition and a cascade ring-opening insertion, which transform into oligomers in situ with molecular weight around 2 × 10 3 g mol −1 . The structures of the subunits and resulting oligopyrazolines are clarified clearly by MALDI-TOF-MS and the quantum yield with excitation at 350 nm is in the range of 12-19%. A cell experiment with HeLa cells demonstrates its promising potential for bioimaging applications. † Electronic supplementary information (ESI) available: The polymerization at different reaction times; 1 H NMR spectrum with the addition of deuteroxide; online FT-IR spectra, FT-IR spectra, MALDI-TOF-MS spectra, DSC curves, TG curves, XRD patterns, SEM images, UV-vis and fluorescent spectra of oligomers; the quantum yield of the obtained oligomers; down-and upconversion fluorescence at different excitation wavelengths and the whole excitation spectrum; cytotoxicity assay. See

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N-(2-Vinyloxyethyl)-4,5-dihydro-1H-pyrazoles

Cited by 4 publications

References 1 publication

Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals

Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals

Synthesis and characterization of fluorescent oligo(3,4,5-triethoxycarbonyl-2-pyrazoline)

One-pot catalyst-free synthesis of down- and upconversion fluorescent oligopyrazolines from diazoacetates and maleic anhydride

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