Arylseleninic acid derivative decomposition towards Se(<scp>ii</scp>)-based electrophiles: an elegant approach to construct 3-selanyl-imidazopyridines

Anghinoni, João M.; Ferreira, Sabrina Souza; Schumacher, Ricardo F.; Iglesias, Bernardo A.; Perin, Gelson; Penteado, Filipe; Lenardão, Eder J.

doi:10.1039/d2nj06086h

Cited by 4 publications

(2 citation statements)

References 60 publications

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“…Based on these results and on our previous advances in the chemistry of BSA, a plausible reaction mechanism was proposed. Initially, the process is fully dependent on a thermal decomposition of BSA 2a toward PhSeSePh 7 .…”

Section: Resultsmentioning

confidence: 99%

“…On the other hand, benzeneseleninic acid (BSA, 2 ) derivatives are inodorous and easy to handle reagents, besides being bench stable, not requiring special storage conditions. Recently, we have devoted our energy to demonstrate the synthetic applicability of BSA as a Se-based reagent to deliver Se(II)-decorated structures, under thermal and photocatalytic conditions, not requiring the use of strong oxidant species, reaction auxiliaries, or additives . Another important feature of BSA is that after the reaction water is the only produced waste.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Selenium-Decorated N-Oxide Isoquinolines: Arylseleninic Acids in Selenocyclization Reactions

Anghinoni,

Ferreira,

Kazmierczak

et al. 2024

J. Org. Chem.

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Herein, we describe the use of benzeneseleninic acid derivatives (BSA) as a bench-stable and easy to handle selenium reagent to access 4-(selanyl)isoquinoline-N-oxides through the selenocyclization of o-alkynyl benzaldehyde oximes. The reaction is conducted in refluxing methanol, allowing the thermal generation of electrophilic selenium species in situ. By this new protocol, a library of 19 selenium-decorated N-oxide isoquinolines was accessed in up to 96% yield with an outstanding substrate tolerance and the feasibility to scale it up 10 times (from 0.25 to 2.5 mmol).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of Selenium-Decorated N-Oxide Isoquinolines: Arylseleninic Acids in Selenocyclization Reactions

Anghinoni,

Ferreira,

Kazmierczak

et al. 2024

J. Org. Chem.

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Benzeneseleninic Acids (BSA) and Photocatalysis: An Alternative Duo for the Synthesis of 3‐Selanylindoles

Quadros,

de Medeiros,

de Oliveira

et al. 2023

Asian J Org Chem

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A novel eco‐friendly methodology for the synthesis of 3‐selanylindoles has been established, circumventing the requirement for transition metal catalysis, strong oxidants and elevated reaction temperatures. In the present protocol a photocatalytic strategy was elegantly developed for the use of benzeneseleninic acids (BSA) derivatives as a selenium‐source reagent, reacting with indoles derivatives, to access 3‐selanylindoles in moderate to good yields. A total of fourteen derivatives were selectively prepared, which among three are unprecedented. In addition to the synthetic advantages, this study gives significant insights into the use of BSA as reagent to construct Se(II)‐decorated products.

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Organoselenium Compounds in Medicinal Chemistry

Gallo‐Rodriguez,

Rodriguez

2024

ChemMedChem

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The chemical and biological interest in this element and the molecules bearing selenium has been exponentially growing over the years. Selenium, formerly designated as a toxin, becomes a vital trace element for life that appears as selenocysteine and its dimeric form, selenocystine, in the active sites of selenoproteins, which catalyze a wide variety of reactions, including the detoxification of reactive oxygen species and modulation of redox activities. From the point of view of drug developments, organoselenium drugs are isosteres of sulfur‐containing and oxygen—containing drugs with the advantage that the presence of the selenium atom confers antioxidant properties and high lipophilicity, which would increase cell membrane permeation leading to better oral bioavailability. This statement is the paramount relevance considering the big number of clinically employed compounds bearing sulfur or oxygen atoms if their structures including nucleosides and carbohydrates. Thus, in this article we have focused on the relevant features of the application of selenium in medicinal chemistry. With the increasing interest in selenium chemistry, we have attempted to highlight the most significant published data on this subject, mainly concentrating the analysis on the last years. In consequence, the recent advances of relevant pharmacological organoselenium compounds are discussed.

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Arylseleninic acid derivative decomposition towards Se(ii)-based electrophiles: an elegant approach to construct 3-selanyl-imidazopyridines

Abstract: Benzeneseleninic acid (BSA) derivatives were used as an alternative, but extremelly useful, source of Se(II)-based electrophiles, generated in situ by thermal decomposition, to construct C-Se bonds, accessing 3-selanylimidazopyridines after reaction...

Cited by 4 publications

References 60 publications

Synthesis of Selenium-Decorated N-Oxide Isoquinolines: Arylseleninic Acids in Selenocyclization Reactions

Synthesis of Selenium-Decorated N-Oxide Isoquinolines: Arylseleninic Acids in Selenocyclization Reactions

Benzeneseleninic Acids (BSA) and Photocatalysis: An Alternative Duo for the Synthesis of 3‐Selanylindoles

Organoselenium Compounds in Medicinal Chemistry

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