Synthesis of benzo[<i>b</i>]chalcogenophenes fused to selenophenes <i>via</i> intramolecular electrophilic cyclization of 1,3-diynes

Hellwig, Paola S.; Guedes, Jonatan S; Barcellos, Angelita M.; Jacob, Raquel G.; Silveira, Cláudio C.; Lenardão, Eder J.; Perin, Gelson

doi:10.1039/d0ob02362k

Cited by 10 publications

(3 citation statements)

References 100 publications

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“…This cyclization was also developed via a radical mechanism with orthoalkynyl selenides, sulfides, anisoles, and diorganyl diselenides, using Oxone as the oxidizing agent. [95,96] In addition, this chemistry was applied to the synthesis of molecules with potential interaction with DNA. [97] We also explored the cyclization reaction using diorganyl diselenides and 2-alkynylphenols as substrates.…”

Section: Organoseleno Cyclization Of Alkynesmentioning

confidence: 99%

“…The reaction conditions were extended to 1,3‐diynyl containing alkyl selenium and alkyl sulfur group at the ortho position to form the selenophene and thiophene derivatives. This cyclization was also developed via a radical mechanism with ortho ‐alkynyl selenides, sulfides, anisoles, and diorganyl diselenides, using Oxone as the oxidizing agent [95,96] . In addition, this chemistry was applied to the synthesis of molecules with potential interaction with DNA [97] …”

Section: Diorganyl Diselenides Promoting Cyclization Reactionsmentioning

confidence: 99%

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Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

do Carmo Pinheiro,

Souza Marques,

Ten Kathen Jung

et al. 2024

The Chemical Record

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Diorganyl diselenides have emerged as privileged structures because they are easy to prepare, have distinct reactivity, and have broad biological activity. They have also been used in the synthesis of natural products as an electrophile in the organoselenylation of aromatic systems and peptides, reductions of alkenes, and nucleophilic substitution. This review summarizes the advancements in methods for the transformations promoted by diorganyl diselenides in the main functions of organic chemistry. Parallel, it will also describe the main findings on pharmacology and toxicology of diorganyl diselenides, emphasizing anti‐inflammatory, hypoglycemic, chemotherapeutic, and antimicrobial activities. Therefore, an examination detailing the reactivity and biological characteristics of diorganyl diselenides provides valuable insights for academic researchers and industrial professionals.

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Section: Organoseleno Cyclization Of Alkynesmentioning

confidence: 99%

Section: Diorganyl Diselenides Promoting Cyclization Reactionsmentioning

confidence: 99%

Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

do Carmo Pinheiro,

Souza Marques,

Ten Kathen Jung

et al. 2024

The Chemical Record

View full text Add to dashboard Cite

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“…As observed above, in the reactions in acetonitrile (Scheme 42), dibutyl telluride 41d and dimethyl disulfide 42b were not suitable dichalcogenides in this reaction, and the formation of products 68l and 68m was not observed, even after 48 h (Scheme 47). The same strategy was used by some of us to access selectively selenophene-fused benzo[b]chalcogenophenes 70, through the intramolecular cyclization of ortho-1,3-diynyl phenyl chalcogenides 69 (Scheme 48) [49]. The optimal conditions were efficiently applied to substituted 1,3-diynes 69 bearing electron-neutral and electron-rich aryl groups, to produce the products 70a-d at excellent yields.…”

Section: Organochalcogen-containing Heterocyclesmentioning

confidence: 99%

Recent Advances in the Oxone-Mediated Synthesis of Heterocyclic Compounds

et al. 2021

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Oxone is a commercially available oxidant, composed of a mixture of three inorganic species, being the potassium peroxymonosulfate (KHSO5) the reactive one. Over the past few decades, this cheap and environmentally friendly oxidant has become a powerful tool in organic synthesis, being extensively employed to mediate the construction of a plethora of important compounds. This review summarizes the recent advances in the Oxone-mediated synthesis of N-, O- and chalcogen-containing heterocyclic compounds, through a wide diversity of reactions, starting from several kinds of substrate, highlighting the main synthetic differences, advantages, the scope and limitations.

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Synthesis of 9,10‐Bis(organochalcogenyl)phenanthrenes by Cyclization of (Biphenyl‐2‐alkyne)chalcogenides

Hellwig,

Goulart,

Guedes

et al. 2024

Asian J Org Chem

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A regioselective, operationally simple and scalable protocol was developed for the synthesis of 9,10‐bis(organochalcogenyl)phenanthrenes and seleno‐spiro[cyclohexane‐1,1'‐indene]‐2,5‐dien‐4‐ones through the cyclization of (biphenyl‐2‐alkyne)chalcogenides. The reaction occurs in the presence of diorganyl diselenides, Oxone® as a green oxidizing agent, and acetonitrile at 80 °C. In this study, 20 compounds were obtained in yields of up to 97% and in short reaction times (1‐4 h).

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Synthesis of benzo[b]chalcogenophenes fused to selenophenes via intramolecular electrophilic cyclization of 1,3-diynes

Abstract: We describe herein an alternative and transition-metal-free procedure for the access of benzo[b]chalcogenophenes fused to selenophenes via intramolecular cyclization of 1,3-diynes promoted by Oxone®.

Cited by 10 publications

References 100 publications

Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

Recent Advances in the Oxone-Mediated Synthesis of Heterocyclic Compounds

Synthesis of 9,10‐Bis(organochalcogenyl)phenanthrenes by Cyclization of (Biphenyl‐2‐alkyne)chalcogenides

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