Visible light-promoted synthesis of 2-aryl-(3-organoselanyl)thieno[2,3-b]pyridines

被引：11

作者：

Bartz, Ricardo Hellwig ^{[1
]}

Peglow, Thiago Jacobsen ^{[1
]}

Penteado, Filipe ^{[1
]}

Jacob, Raquel Guimaraes ^{[1
]}

Lenardao, Eder Joao ^{[1
]}

Perin, Gelson ^{[1
]}

机构：

[1] Univ Fed Pelotas UFPel, Ctr Ciencias Quim Farmaceut & Alimentos CCQFA, Lab Sintese Organ Limpa LASOL, POB 354, BR-96010900 Pelotas, RS, Brazil

来源：

GREEN CHEMISTRY LETTERS AND REVIEWS | 2022年 / 15卷 / 02期

关键词：

Organochalcogen; thieno[2; 3-b]pyridines; green chemistry; visible light-promoted reaction; heterocycles; selenocyclization; ORGANOSELENIUM CHEMISTRY; NITROGEN-HETEROCYCLES; COGNITIVE IMPAIRMENT; SELECTIVE INHIBITORS; SMALL MOLECULES; DERIVATIVES; SELENIUM; DRUGS; ANTIOXIDANT; DISCOVERY;

D O I：

10.1080/17518253.2022.2065891

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We describe a simple and environment-friendly visible light-promoted protocol to access 2-aryl-(3-organoselanyl)thieno[2,3-b]pyridines, through the selenocyclization of 3-(arylethynyl)-2-(alkylthio)pyridines in the presence of diorganyl diselenides as selenium source. The Se-based reactive species were generated in situ by the homolytic Se-Se bond cleavage using blue LED in an O-2 atmosphere at room temperature. The protocol was suitable for a wide range of substrates bearing different substituents, allowing the synthesis of twenty-one thieno[2,3-b]pyridines in good to excellent yields (57-99%).

引用

页码：372 / 381

页数：10

共 68 条

[1] Development of Small Molecules with a Noncanonical Binding Mode to HIV-1 Trans Activation Response (TAR) RNA [J].

Abulwerdi, Fardokht A. ;

Shortridge, Matthew D. ;

Sztuba-Solinska, Joanna ;

Wilson, Robert ;

Le Grice, Stuart F. J. ;

Varani, Gabriele ;

Schneekloth, John S., Jr. .

JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (24) :11148-11160

[2] Synthesis and Antimicrobial Evaluation of Some Novel Bis-α,β-Unsaturated Ketones, Nicotinonitrile, 1,2-Dihydropyridine-3-carbonitrile, Fused Thieno[2,3-b]pyridine and Pyrazolo[3,4-b]pyridine Derivatives [J].

Altalbawy, Farag M. A. .

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2013, 14 (02) :2967-2979

[3]

Alvarez-Builla J., 2010, MODERN HETEROCYCLIC

[4]

Anastas P.T., 1998, Green Chemistry: Theory and Practice, VI

[5] Green Chemistry: Principles and Practice [J].

Anastas, Paul ;

Eghbali, Nicolas .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :301-312

[6] Sustainability Assessment of Mechanochemistry by Using the Twelve Principles of Green Chemistry [J].

Ardila-Fierro, Karen J. ;

Hernandez, Jose G. .

CHEMSUSCHEM, 2021, 14 (10) :2145-2162

[7] Antidepressant-like effect of a new selenium-containing compound is accompanied by a reduction of neuroinflammation and oxidative stress in lipopolysaccharide-challenged mice [J].

Casaril, Angela M. ;

Domingues, Micaela ;

Fronza, Mariana ;

Vieira, Beatriz ;

Begnini, Karine ;

Lenardao, Eder J. ;

Seixas, Fabiana K. ;

Collares, Tiago ;

Nogueira, Cristina W. ;

Savegnago, Lucielli .

JOURNAL OF PSYCHOPHARMACOLOGY, 2017, 31 (09) :1263-1273

[8] Anhedonic- and anxiogenic-like behaviors and neurochemical alterations are abolished by a single administration of a selenium-containing compound in chronically stressed mice [J].

Casaril, Angela Maria ;

Lourenco, Darling de Andrade ;

Domingues, Micaela ;

Smaniotto, Thiago Angelo ;

Birmann, Paloma Taborda ;

Vieira, Beatriz ;

Sonego, Mariana Souza ;

Seixas, Fabiana Kommling ;

Collares, Tiago ;

Lenardao, Eder Joao ;

Savegnago, Lucielli .

COMPREHENSIVE PSYCHONEUROENDOCRINOLOGY, 2021, 6

[9] 3-[(4-chlorophenyl)selanyl]-1-methyl-1H-indole ameliorates long-lasting depression- and anxiogenic-like behaviors and cognitive impairment in post-septic mice: Involvement of neuroimmune and oxidative hallmarks [J].

Casaril, Angela Maria ;

Domingues, Micaela ;

Lourenco, Darling de Andrade ;

Vieira, Beatriz ;

Begnini, Karine ;

Corcini, Carine Dahl ;

Franca, Raqueli Teresinha ;

Varela Junior, Antonio Sergio ;

Seixas, Fabiana Kommling ;

Collares, Tiago ;

Lenardao, Eder Joao ;

Savegnago, Lucielli .

CHEMICO-BIOLOGICAL INTERACTIONS, 2020, 331

[10] The antioxidant and immunomodulatory compound 3-[(4-chlorophenyl) selanyl]-1-methyl-1H-indole attenuates depression-like behavior and Cognitive impairment developed in a mouse model of breast tumor [J].

Casaril, Angela Maria ;

Domingues, Micaela ;

Bampi, Suely Ribeiro ;

Lourenco, Darling de Andrade ;

Smaniotto, Thiago Angelo ;

Segatto, Natalia ;

Vieira, Beatriz ;

Seixas, Fabiana K. ;

Collares, Tiago ;

Lenardao, Eder Joao ;

Savegnago, Lucielli .

BRAIN BEHAVIOR AND IMMUNITY, 2020, 84 :229-241

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