Direct synthesis of 2-aryl-1,3-benzoselenazoles by reaction of bis(2-aminophenyl) diselenides with aryl aldehydes using sodium metabisulfite

Radatz, Cátia S.; Alves, Diego; Schneider, Paulo H.

doi:10.1016/j.tet.2012.11.091

Cited by 47 publications

(27 citation statements)

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“…Inspired by the synthetic route developed by Christiaens and co-workers, [40] we focused our attentiono nt he dehydra- Scheme1.The different synthetic approaches toward the preparation of 2-functionalised benzoselenazole derivatives startingf rom:a )2-selenoanilides (R 1 = Me or aryl;R 2 = Me or Et); [40] b) bis(2-aminophenyl)diselenide (R 1 = alkyl or aryl); [44,45] c) 2-iodoanilides (R 1 = alkyl, aryl or heteroaryl);and [47] d) 2-iodoaniline (R 1 = aryl or heteroaryl). [48] tive cyclization reaction to preparet he targeted 2-substituted chalcogenazole derivatives.…”

Section: Synthesismentioning

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 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%

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

Kremer

Fermi

Biot

et al. 2016

Chemistry A European J

115

112

View full text Add to dashboard Cite

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“…However, the method could not be used to furnish products from alkyl aldehydes. These reactions were conducted under conventional heating as well as under microwave irradiation, because the use of focused microwave irradiation was found to drastically decrease the reaction time 9f…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, until now, 2‐alkyl‐1,3‐benzoselenazoles could not be achieved by the available synthetic tools. In this context, our interest on the synthesis of organoselenium compounds9f,12 prompted us to explore a general procedure with which to obtain 2‐substituted 1,3‐benzoselenazoles from bis(2‐aminophenyl) diselenide and carboxylic acids by using tributylphosphine under conventional heating or microwave irradiation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2‐Substituted 1,3‐Benzoselenazoles from Carboxylic Acids Promoted by Tributylphosphine

et al. 2014

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We report a general, practical, and simple metal-free method for the synthesis of 2-substituted 1,3-benzoselenazoles by the reaction of bis(2-aminophenyl)diselenide with a wide range of carboxylic acids, promoted by tributylphosphine. This efficient reaction furnishes 2-aryl-1,3-benzoselenazoles in good yields and tolerates a variety of substituents at the aryl moiety of carboxylic acids. For the first time, 2-alkyl-1,3-

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“…2 Besides, the synthesis of 2-substituted-1,3-benzothiazoles have attracted much attention according to their notably photophysical properties. 3 Our continuing interest on the synthesis of organoselenium compounds 4 prompted us to explore a general procedure to obtain 2-substituted 1,3-benzoselenazoles from bis(2-aminophenyl) diselenide (1a) and carboxylic acids (2a-m), using tributylphosphine in toluene under conventional heating or microwave irradiation (scheme 1). Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-aryl-1,3-benzoselenazoles from bis(2- aminophenyl) diselenides and carboxylic acids using PBu3

Radatz¹,

Rampon²,

Balaguez³

et al. 2013

Proceedings of the 15th Brazilian Meeting on Organic Synthesis Proceedings

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Direct synthesis of 2-aryl-1,3-benzoselenazoles by reaction of bis(2-aminophenyl) diselenides with aryl aldehydes using sodium metabisulfite

Cited by 47 publications

References 100 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

Synthesis of 2‐Substituted 1,3‐Benzoselenazoles from Carboxylic Acids Promoted by Tributylphosphine

Synthesis of 2-aryl-1,3-benzoselenazoles from bis(2- aminophenyl) diselenides and carboxylic acids using PBu3

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