Straightforward access to oxazaborines, diazaborinones and triazaborines by reactions of β-enaminoamides with 4-methylbenzenediazonium tetraphenylborate

Svobodová, Markéta; Bárta, Jan; Šimůnek, Petr; Bertolasi, Valerio; Macháček, Vladimı́r

doi:10.1016/j.jorganchem.2008.10.004

Cited by 20 publications

(8 citation statements)

References 55 publications

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“…On the other hand, the boron signal of OxaBo2 (Figure S15), having diphenylboron moiety, is a broad singlet. This was observed also for other similar compounds . Chemical shift 2.6 ppm lies in the range typical for this kind of compounds and its value also evidences for rather less crowded environment around the boron atom which can be explained by small hydrogen substituent on the nitrogen …”

Section: Resultssupporting

confidence: 78%

Photophysical and Electrochemiluminescence of Coumarin‐Based Oxazaborines

et al. 2020

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We describe the synthesis, electrochemistry, photophysics, computational analysis and electrochemiluminescence (ECL) of a new series of oxazaborine molecules. Our strategy is based on the modification of the coumarin-oxazaborine moiety to be directly joined through a carbon-carbon bond, forming donoracceptor (D-A) chromophores. These new structures substantially change the electron distribution as well as photophysical and electrochemical behaviors with a strong effect on the final quantum yield. For all compounds, we observed a very high PL quantum yield (70-75 %) and relatively accessible first oxidation and first reduction. All of these characteristics allow us to study the ECL of these molecules, obtaining a very high ECL efficiency that is four times higher than the standard dyes, opening the application of oxazaborine as bright ECL luminophores.

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Section: Resultssupporting

confidence: 78%

Photophysical and Electrochemiluminescence of Coumarin‐Based Oxazaborines

et al. 2020

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“…We have studied the reactions of polarized ethylenes, such as β-enaminones, β-enaminonitriles, and β-enaminoamides, with substitution on the amino group, with diazonium salts, leading to heterocyclic compounds. These compounds are pyridazines [20][21][22], pyrazoles [23][24][25][26], oxazaborines, diazaborinones, and triazaborines [27][28][29][30][31]. In 2009, we published work on the reaction of β-enaminoamides 1 (Figure 1, R 3 = Ph) and 4-methylbenzenediazonium tetraphenylborate to give compounds I-III (Scheme 2) [28].…”

Section: Introductionmentioning

confidence: 99%

“…These compounds are pyridazines [20][21][22], pyrazoles [23][24][25][26], oxazaborines, diazaborinones, and triazaborines [27][28][29][30][31]. In 2009, we published work on the reaction of β-enaminoamides 1 (Figure 1, R 3 = Ph) and 4-methylbenzenediazonium tetraphenylborate to give compounds I-III (Scheme 2) [28]. The ring transformation of compound I to diazaborinones II (predominantly when R 1 = Me) and triazaborines III (predominantly when R 1 = H) was proceeded under reflux in N,N-dimethylformamide [28].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of New Boron Compounds Using Reaction of Diazonium Tetraphenylborate with Enaminoamides

Svobodová

Svoboda

et al. 2022

Molecules

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A family of oxazaborines, diazaborinones, triazaborines, and triazaborinones was prepared by reaction of polarized ethylenes, such as β-enaminoamides, with 4-methylbenzenediazonium tetraphenylborates. The reaction conditions (stirring in CH2Cl2 at room temperature (Method A) or stirring with CH3COONa in CH2Cl2 at room temperature (Method B) or refluxing in the CH2Cl2/toluene mixture (Method C)) controlled the formation and relative content of these compounds in the reaction mixtures from one to three products. Substituted oxazaborines gradually rearranged into diazaborinones at 250 °C. The prepared compounds were characterized by 1H NMR, 13C NMR, IR, and UV–Vis spectroscopy, HRMS, or microanalysis. The structure of individual compounds was confirmed by 11B NMR, 15N NMR, 1D NOESY, and X-ray analysis. The mechanism of reaction of enaminoamides with 4-methylbenzenediazonium tetraphenylborate was proposed.

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“…β‐Ketoanilides are versatile reagents that have been extensively utilized in heterocyclic synthesis . In this work, the prepared heterocycles are proved to be interesting for their potentiality as biodegradable agrochemicals , pharmaceuticals , as non‐peptide HIV , protease inhibitors, anti‐schistosomal agents , and intermediates for the manufacture of dyestuffs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some New Thiazolo[3,2‐a]pyrimidine Derivatives and Their Applications as Disperse Dyes

Elmaaty

El‐Taweel

Abdeldayem

et al. 2019

Journal of Heterocyclic Chem

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A series of novel thiazolo[3,2‐a]pyrimidine derivatives were synthesized by using β‐ketoanilides 1a–c as starting materials and as key intermediates for preparation of new pyrimidinecompounds 3a–e and fused heterocyclic pyrimidine derivatives 5a–c. The new compounds were transformed to disperse dyes 6a,b and 7. The chemical structures were elucidated by spectroscopic and elemental analyses and found to be in good agreement with the proposed structures. The versatility of compounds 6a,b and 7 for textile dyeing as disperse dyes was reported. The synthesized dyes were applied to polyester fabrics by using high temperature dyeing method at 120°C. The dye uptake expressed as color strength (k/s) of the dyed samples has been measured. Moreover, the color strength was examined in detail. In addition, the position of color in CIELAB coordinates (L*, a*, b*, h, and C*) was assessed. The color fastness of the dyed samples gave excellent results for washing and rubbing; however, the light fastness was moderate. Raman spectra of dyed samples unequivocally excluded ring dyeing and found to match with the proposed structures.

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Straightforward access to oxazaborines, diazaborinones and triazaborines by reactions of β-enaminoamides with 4-methylbenzenediazonium tetraphenylborate

Cited by 20 publications

References 55 publications

Photophysical and Electrochemiluminescence of Coumarin‐Based Oxazaborines

Photophysical and Electrochemiluminescence of Coumarin‐Based Oxazaborines

Synthesis and Characterization of New Boron Compounds Using Reaction of Diazonium Tetraphenylborate with Enaminoamides

Synthesis of Some New Thiazolo[3,2‐a]pyrimidine Derivatives and Their Applications as Disperse Dyes

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