Synthesis of 5<i>H</i>‐Selenopheno[3,2‐<i>c</i>]isochromen‐5‐ones Promoted by Dialkyl Diselenides and Oxone®

Goulart, Helen A.; Neto, José S. S.; Barcellos, Angelita M.; Barcellos, Thiago; Silva, Márcio S.; Alves, Diego; Jacob, Raquel G.; Lenardão, Eder J.; Perin, Gelson

doi:10.1002/adsc.201900288

Cited by 30 publications

(37 citation statements)

References 64 publications

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“…The alkylselenium substitution of selenophenefused chromenes and isochromenones has the potential to act as a substrate in Suzuki and Sonogashira-type cross coupling reactions and ring opening transformation using n-butyl lithium to give biologically diversified products. [83] In another method, selenophenes were synthesized from 1,3-enynes 27 and selenium under ClCF 2 H (freon) atmosphere which acts as an economic difluoromethylating agent (Scheme 12). The method was originally optimized for the synthesis of difluoromethylthiolated thiophene derivatives and then extended for the construction of difluoromethylselenylated selenophene analogues 28.…”

Section: Selenocyclofunctionalization Of Unsaturated Synthetic Intermmentioning

confidence: 99%

Insights into the Recent Synthetic Advances of Organoselenium Compounds

2021

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The ever-growing interest for organoselenium compounds amongst the chemists has made commendable impact in the field of medicinal chemistry, material chemistry, chemical biology and biochemistry. Researchers have progressively contributed in the development of organoselenium compounds over the years which has been periodically reviewed. On the similar note, this review attempts at providing an overview of the recent advances made in organoselenium chemistry while covering their catalytic indulgence in different transformational approaches, their role in asymmetric synthesis, and synthetic approaches steering their synthesis. These approaches encompass selenofunctionalization and/or cyclization, electrochemical selenylation, bromolactonization, [2,3]-or [1,2]-sigmatropic rearrangement reactions among others. Herein, we have focused on the synthetic approaches developed for the past three years that have not been covered in previously reviewed scientific material. With the knowledge of the recent progress covered, this review could contribute towards future development of organoselenium compounds along with the improvement of the current status.

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Section: Selenocyclofunctionalization Of Unsaturated Synthetic Intermmentioning

confidence: 99%

Insights into the Recent Synthetic Advances of Organoselenium Compounds

2021

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“…[147] The cascade intramolecular cyclization of methyl 2-(organyl-1,3-diynyl)benzoate 265 promoted by electrophilic selenium source generated in situ by the reaction of dialkyl diselenides 4 with Oxone ® , using ethanol as solvent, successfully afforded the cyclized isochrome- nones fused to selenophenes, 5H-selenopheno [3,2-c] isochromen-5-ones 266 (Scheme 87). [148] The preparations of linear and angular heteroacenes were successfully achieved by terminal alkynes 267 in two steps. Linear heteroacenes 270 are formed from the homocoupling of alkynes 268, while angular heteroacenes were successfully achieved by homocoupling of alkynes 269.…”

Section: Electrophilic Cyclization Of 13-diyne and 135-triynementioning

confidence: 99%

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Sonawane

Ninomiya

et al. 2020

Adv Synth Catal

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containing heterocyclic scaffolds by virtue of their interesting reactivities and a broad range of applications in the medicinal and materials chemistry. This review involves the electrophilic/radical cyclization of alkynes containing heteroatoms which resulted into the novel Se‐heterocycles. The synthesis of seleno‐heterocycles via different nucleophiles including O, N, S, Se, Te, and C‐nucleophiles is exhaustively discussed. Also, one‐pot electrophilic cyclization of 1,3‐diynes and 1,3,5‐triynes was described in details. Furthermore, the various mechanisms underlying the synthesis of selenium‐β‐lactam, carbapenem heterocycle, bis‐ and tris‐selenide alkene, β‐selenosulfonation and selenated alkynes were discussed. The Se‐heterocycles reported in this review allow preparing these selenated compounds bearing the selenium moiety both on the rings (outside) and inside the ring (e. g. selenophenes). The review demonstrates the growing opportunities to construct selenium containing heterocycles from alkynes containing heteroatoms.

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“…However, when the dimer dimethyl 2,2′-(buta-1,3-diyne-1,4-diyl)dibenzoate was submitted the optimal conditions in the reaction with Bu2Se2, the double intramolecular O-cyclization product was not formed, and the fused isochromenones selenophene 181k was obtained in 80% yield after 1.5 h. The presence of a fluorgroup at the pendant ring of the ester group in 180l (R = F) did not alter the reactivity, affording the respective selenophene 181l in 84% yield after 2.5 h (Scheme 124). In 2019, some of us [188] reported the synthesis of 5-H-selenopheno[3,2-c]isochromen-5-ones 181 through a double intramolecular cyclization of methyl 2-(organyl-1,3-diynyl)benzoate 180 promoted by electrophilic species of selenium generated in situ by the reaction of dialkyl diselenides with Oxone ® , under the reflux of EtOH, in an open flask (Scheme 124). This protocol was suitable for different dialkyl diselenides (R 2 = Bu, Et, Oct), which reacted with the diyne 180 to give the expected isochromenones 181a-c in 77-86% yields, while no reaction was observed starting from dibenzyland bis(2-naphthylmethyl)diselenide.…”

Section: Scheme 123 Suzuki Cross-coupling Reactions Of 176a and 178amentioning

confidence: 99%

“…In 2019, some of us [ 188 ] reported the synthesis of 5- H- selenopheno[3,2- c ]isochromen-5-ones 181 through a double intramolecular cyclization of methyl 2-(organyl-1,3-diynyl)benzoate 180 promoted by electrophilic species of selenium generated in situ by the reaction of dialkyl diselenides with Oxone ® , under the reflux of EtOH, in an open flask ( Scheme 124 ). This protocol was suitable for different dialkyl diselenides (R 2 = Bu, Et, Oct), which reacted with the diyne 180 to give the expected isochromenones 181a - c in 77–86% yields, while no reaction was observed starting from dibenzyl- and bis(2-naphthylmethyl)diselenide.…”

Section: Fused Selenophenes and Benzoselenophenesmentioning

confidence: 99%

Recent Advances in the Synthesis of Selenophenes and Their Derivatives

et al. 2020

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The selenophene derivatives are an important class of selenium-based heterocyclics. These compounds play an important role in prospecting new drugs, as well as in the development of new light-emitting materials. During the last years, several methods have been emerging to access the selenophene scaffold, employing a diversity of cyclization-based synthetic strategies, involving specific reaction partners and particularities. This review presents a comprehensive discussion on the recent advances in the synthesis of selenophene-based compounds, starting from different precursors, highlighting the main differences, the advantages, and limitations among them.

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Synthesis of 5H‐Selenopheno[3,2‐c]isochromen‐5‐ones Promoted by Dialkyl Diselenides and Oxone®

Cited by 30 publications

References 64 publications

Insights into the Recent Synthetic Advances of Organoselenium Compounds

Insights into the Recent Synthetic Advances of Organoselenium Compounds

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Recent Advances in the Synthesis of Selenophenes and Their Derivatives

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