Organotellurium Chemistry: Remarkably Facile Preparation of Benzo‐1,3‐tellurazoles

McMullen, Nathan C.; Fronczek, Frank R.; Junk, Thomas

doi:10.1002/jhet.1007

Cited by 17 publications

(17 citation statements)

References 11 publications

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“…[48] In the case of the benzotellurazoles analogues,t he synthetic protocols are scarcer. [40][41][42][43][49][50][51] To the best of our knowledge,t he developed methodst od ate (Scheme 2) are limitedt ot he preparation of 2-substituteda lkyl and aryl derivatives.T his exploits the dehydrative cyclization of 2-telluroanilides with either phosphorus oxychloride, [40,42,43,49] phosphorus trichloride [41] or hypophosphorus acid, [50,51] with the latter conditions only compatible for the synthesis of alkyl and aryl 2substituted derivatives.…”

Section: Synthesismentioning

confidence: 99%

“…Comparative absorption spectra of compounds 11 Y -19 Y in CH 2 Cl 2 are shown in Figures 4, 5, and 6( see also the Supporting Information), with the keya b-Scheme2.Synthetic approach for the preparation of 2-functionalised benzotellurazole derivatives (R 1 = alkyl or aryl). [40][41][42][43][49][50][51] [33] Differently, 19 Se and its analogue 19 Te show ab road and low intense absorption band in the visible region,at ypical electronic transition fingerprinting the ferrocene unit ( Figure 6). For both benzochalcogenazoles, an arrow band is recorded with e values between 15 000 and 23 000 m À1 cm À1 at higher l (comprised between 235 and 265 nm), likely corresponding to the electronic transition centred on the phenyl unit.…”

Section: Steady-state Uv/vis Absorption and Emission Studies In Solutionmentioning

confidence: 99%

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Supramolecular Wiring of Benzo‐1,3‐chalcogenazoles through Programmed Chalcogen Bonding Interactions

Kremer

Fermi

Biot

et al. 2016

Chemistry A European J

115

112

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The high-yielding synthesis of 2-substituted benzo-1,3-tellurazoles and benzo-1,3-selenazoles through a dehydrative cyclization reaction has been reported, giving access to a large variety of benzo-1,3-chalcogenazoles. Exceptionally, these aromatic heterocycles proved to be very stable and thus very handy to form controlled solid-state organizations in which wire-like polymeric structures are formed through secondary N⋅⋅⋅Y bonding interactions (SBIs) engaging the chalcogen (Y=Se or Te) and nitrogen atoms. In particular, it has been shown that the recognition properties of the chalcogen centre at the solid state could be programmed by selectively barring one of its σ-holes through a combination of electronic and steric effects exerted by the substituent at the 2-position. As predicted by the electrostatic potential surfaces calculated by quantum chemical modelling, the pyridyl groups revealed to be the stronger chalcogen bonding acceptors, and thus the best ligand candidate for programming the molecular organization at the solid state. In contrast, the thiophenyl group is an unsuitable substituent for establishing SBIs in this molecular system as it gives rise to chalcogen-chalcogen repulsion. The weaker chalcogen donor properties of the Se analogues trigger the formation of feeble N⋅⋅⋅Se contacts, which are manifested in similar solid-state polymers featuring longer nitrogen-chalcogen distances.

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Section: Synthesismentioning

confidence: 99%

Section: Steady-state Uv/vis Absorption and Emission Studies In Solutionmentioning

confidence: 99%

Supramolecular Wiring of Benzo‐1,3‐chalcogenazoles through Programmed Chalcogen Bonding Interactions

Kremer

Fermi

Biot

et al. 2016

Chemistry A European J

115

112

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“…The few reported compounds comprise a small number of benzotellurazine derivatives (Detty & O'Regan, 1994). Of these, only 10H-phenotellurazine (Junk & Irgolic, 1989) and 1,1-dichloro-1,1-dihydro-2H-1,4-benzotellurazin-3(4H)-one (McMullen et al, 2013) were characterized by X-ray crystallography. Even fewer seven-membered Te-N heterocycles are known.…”

Section: Introductionmentioning

confidence: 99%

“…Even fewer seven-membered Te-N heterocycles are known. The preparation of 2H-1,4-benzotellurazin-3(4H)-one, (I), has been reported twice (Sadekov et al, 1993;McMullen et al, 2013), but no structural parameters were published. In addition, 11-(4-methylphenyl)dibenzo [b,f]- [1,4]tellurazepine was prepared (Ladatko et al, 1987) but not structurally characterized.…”

Section: Introductionmentioning

confidence: 99%

The first crystal structures of six- and seven-membered tellurium- and nitrogen-containing (Te—N) heterocycles: 2H-1,4-benzotellurazin-3(4H)-one and 2,3-dihydro-1,5-benzotellurazepin-4(5H)-one

2016

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There is a paucity of data concerning the structures of six- and seven-membered tellurium- and nitrogen-containing (Te-N) heterocycles. The title compounds, C8H7NOTe, (I), and C9H9NOTe, (II), represent the first structurally characterized members of their respective classes. Both crystallize with two independent molecules in the asymmetric unit. When compared to their sulfur analogs, they exhibit slightly greater deviations from planarity to accommodate the larger chalcogenide atom, with (II) adopting a pronounced twist-boat conformation. The C-Te-C angles of 85.49 (15) and 85.89 (15)° for the two independent molecules of (I) were found to be somewhat smaller than those of 97.4 (2) and 97.77 (19)° for the two independent molecules of (II). The C-Te bond lengths [2.109 (4)-2.158 (5) Å] are in good agreement with those predicted by the covalent radii. Intermolecular N-H...O hydrogen bonding in (I) forms centrosymmetric R2(2)(8) dimers, while that in (II) forms chains. In addition, intermolecular Te...O contacts [3.159 (3)-3.200 (3) Å] exist in (I).

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“…Bis(2-aminophenyl) ditelluride and bis(2-amino-5-methyl) ditelluride were prepared as previously reported [14]. All other chemicals were purchased from Fisher Scienti c and used as received.…”

Section: Methodsmentioning

confidence: 99%

10H-Pyrazino[2,3-b][1,4]benzotellurazine, a Novel Tellurium-Containing Heterocyclic System

Smith

Alexis

Fronczek

et al. 2020

Heteroatom Chemistry

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Condensation of 2,3-dichloropyrazine with 2-aminobenzenetellurole and 2-amino-5-methylbenzenetellurole, generated in situ by reduction of the corresponding ditellurides, resulted in the formation of novel 10H-pyrazino[2,3-b][1,4]benzotellurazine and its 7-methyl derivative. The products were purified via their well-crystallized 5,5-dibromo derivatives. X-ray crystallographic analysis of the title compound indicates that it has a pronounced V-shape and forms hydrogen-bonded dimers. Te, N-containing heterocycles have the potential of offering access to supramolecular assemblies.

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Organotellurium Chemistry: Remarkably Facile Preparation of Benzo‐1,3‐tellurazoles

Cited by 17 publications

References 11 publications

Supramolecular Wiring of Benzo‐1,3‐chalcogenazoles through Programmed Chalcogen Bonding Interactions

Supramolecular Wiring of Benzo‐1,3‐chalcogenazoles through Programmed Chalcogen Bonding Interactions

The first crystal structures of six- and seven-membered tellurium- and nitrogen-containing (Te—N) heterocycles: 2H-1,4-benzotellurazin-3(4H)-one and 2,3-dihydro-1,5-benzotellurazepin-4(5H)-one

10H-Pyrazino[2,3-b][1,4]benzotellurazine, a Novel Tellurium-Containing Heterocyclic System

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