A facile access to new diazepines derivatives: Spectral characterization and crystal structures of 7-(thiophene-2-yl)-5-(trifluoromethyl)-2,3-dihydro-1 H -1,4-diazepine and 2-thiophene-4-trifluoromethyl-1,5-benzodiazepine

Ahumada, Guillermo; Carrillo, David; Manzur, Carolina; Fuentealba, Mauricio; Roisnel, Thierry; Hamon, Jean‐René

doi:10.1016/j.molstruc.2016.07.047

Cited by 13 publications

(4 citation statements)

References 39 publications

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“…Consequently, the CO (coupled with the C10C11) stretching mode was assigned to the strong band at 1635 cm −1 in the IR spectrum. 35 The broad absorption located at 3242 cm −1 is attributed to the N2−H stretching of the diazepine group, which is blue-shifted compared to the N− H stretching modes in 1,4-diazepine derivatives, 36 indicating that the intermolecular N2−H•••O1 hydrogen bonds affect the force constant of the N−H group. The medium intensity IR band located at 1540 cm −1 is attributed to the C−N stretching vibration of the diazepine ring.…”

Section: Resultsmentioning

confidence: 99%

Enol-imino–Keto-enamine Tautomerism in a Diazepine Derivative: How Decisive Are the Intermolecular Interactions in the Equilibrium?

et al. 2019

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The strange tautomeric equilibrium behaviour exhibited by a new o-hydroxyphenyl diazepine derivative, when the compound is analysed both in solution and solid state, open the structural study of the enol-imino-keto-enamine forms and the influence of the intermolecular interactions in their equilibrium. The expected enol-imino form, in which the enol is part of a phenyl system and a strong O-H ... N intramolecular hydrogen bond is established, results the most stable tautomer in gas phase (theoretical calculations) and was detected by NMR spectroscopy when the compound was dissolved in aprotic solvents. Nevertheless, the keto-enamine form in which the keto group integrate a cyclohexadienone moiety and the aromaticity of the phenol is loss, was the only tautomer in the crystal lattice according to single-crystal X-ray diffraction, vibrational spectroscopy and diffuse reflectance results. The last form was also found as the main tautomer in UV-Vis and NMR spectroscopy, when a protic solvent was employed.

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Section: Resultsmentioning

confidence: 99%

Enol-imino–Keto-enamine Tautomerism in a Diazepine Derivative: How Decisive Are the Intermolecular Interactions in the Equilibrium?

et al. 2019

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“…Initially, the deacylation of 2‐(2‐phenylethyl)‐1‐phenylbutane‐1,3‐dione ( 1 a ) was optimized using a variety of promoters 2 (Table 1). For this purpose, simple diamine chains were investigated first, including ethylenediamine ( 2 a ), [21a,32] propane‐1,3‐diamine ( 2 b ), [33] and butane‐1,4‐diamine ( 2 c ) (Table 1, entries 1–3). In these cases, high yields of deacetylated ketone 3 a were obtained, and a small amount of debenzoylated ketone 4 a was also obtained (<9 % yield).…”

Section: Resultsmentioning

confidence: 99%

Diamine‐Promoted Deacylation of 2‐Alkyl‐1,3‐Diketones for the Facile Synthesis of Ketones

et al. 2022

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A facile synthesis of ketones was developed based on the diamine‐promoted deacylation of 2‐alkyl‐1,3‐diketones. More specifically, 2‐alkyl‐1‐arylbutane‐1,3‐diones were efficiently deacylated in the presence of 2,2‐dimethylpropane‐1,3‐diamines to afford the corresponding aryl ketones with a high regioselectivity. Notably, this regioselectivity was different from that observed under the conventional retro‐Claisen conditions.

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“…The synthesis and biological activity applications of the diazepine skeleton, which has seven rings and contains two nitrogen atoms, in heterocyclic chemistry is particularly noticeable in multi-ring and hybrid structures [6]. Diazepine skeleton has been an active ingredient in anxiolytic, sedative and anticonvulsant drugs for a long time.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel hybrid compounds containing coumarin and benzodiazepine rings based on dye

Gümüş

2021

Journal of Heterocyclic Chem

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Coumarin derivatives, one of the organic fluorescent materials, are widely applied in many areas such as laser dyes, organic light emitting diodes (OLED), pharmaceuticals and bio/chemosensors, with the advantages of the large conjugated system and planar structure. In the coumarin analogs, which are polarity sensitive fluorophores, a shift to the red zone is observed in the case of π expansion at 3-positions and electron donor groups at 7-positions. The present article reports the synthesis of novel hybrid compounds (CD1-CD8) containing coumarin and benzodiazepine rings using ethyl 3-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)-3-oxopropanoate reagent and 1,2-diaminobenzene derivatives under optimized reaction conditions with PTSA catalyst. The structures of target compounds synthesized were characterized by FTIR, 1 HNMR, 13 CNMR, HRMS and UV-Vis spectra. The effects of electron withdrawing and electron donor groups in the cyclocondensation reaction that takes place as regioselective were evaluated in detail. The substituent effects were investigated for n-π* and π-π* electronic transitions in UV-Vis Spectroscopy.

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A facile access to new diazepines derivatives: Spectral characterization and crystal structures of 7-(thiophene-2-yl)-5-(trifluoromethyl)-2,3-dihydro-1 H -1,4-diazepine and 2-thiophene-4-trifluoromethyl-1,5-benzodiazepine

Cited by 13 publications

References 39 publications

Enol-imino–Keto-enamine Tautomerism in a Diazepine Derivative: How Decisive Are the Intermolecular Interactions in the Equilibrium?

Enol-imino–Keto-enamine Tautomerism in a Diazepine Derivative: How Decisive Are the Intermolecular Interactions in the Equilibrium?

Diamine‐Promoted Deacylation of 2‐Alkyl‐1,3‐Diketones for the Facile Synthesis of Ketones

Synthesis and characterization of novel hybrid compounds containing coumarin and benzodiazepine rings based on dye

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