Arylseleninic acid as a green, bench-stable selenylating agent: synthesis of selanylanilines and 3-selanylindoles

被引:17
作者
Abenante, Laura [1 ]
Padilha, Nathalia B. [1 ]
Anghinoni, Joao M. [1 ]
Penteado, Filipe [1 ]
Rosati, Ornelio [2 ]
Santi, Claudio [2 ]
Silva, Marcio S. [1 ]
Lenardao, Eder J. [1 ]
机构
[1] Univ Fed Pelotas UFPel, LASOL CCQFA, POB 354, BR-96010900 Pelotas, RS, Brazil
[2] Univ Perugia, Dept Pharmaceut Sci, Grp Catalysis Synth & Organ Green Chem, Via Liceo 1, I-06123 Perugia, PG, Italy
关键词
METAL-FREE SYNTHESIS; ANTIOXIDANT ACTIVITY; ANTIDEPRESSANT-LIKE; SELENIUM; OXIDATION; OLEFINS; ARENES; PHENYLSELENYLATION; CYCLIZATION; CONVERSION;
D O I
10.1039/d0ob01073a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Arylseleninic acids were used as an electrophilic selenium source in aromatic substitution reactions, usingN,N-substituted anilines and indoles as nucleophiles at 70 degrees C for 6-15 h. A total of fourteen 4-selanylanilines and five 3-selanylindoles were selectively obtained in good to excellent yields. The starting benzeneseleninic acids are easily prepared from the respective diselenides, are bench stable and easy to handle, affording water as the only waste at the end of the reaction.
引用
收藏
页码:5210 / 5217
页数:8
相关论文
共 73 条
[1]   Selenium containing heterocycles: Synthesis, anti-inflammatory, analgesic and anti-microbial activities of some new 4-cyanopyridazine-3(2H)selenone derivatives [J].
Abdel-Hafez, Sh. H. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (09) :1971-1977
[2]   Biomimetic seleninates and selenonates [J].
Abdo, Mohannad ;
Knapp, Spencer .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9234-+
[3]   Electrophilic Aromatic Selenylation: New OPRT Inhibitors [J].
Abdo, Mohannad ;
Zhang, Yong ;
Schramm, Vern L. ;
Knapp, Spencer .
ORGANIC LETTERS, 2010, 12 (13) :2982-2985
[4]  
Alberto E. E., 2011, Selenium and Tellurium Chemistry from Small Molecules to Biomolecules and Materials, P251, DOI DOI 10.1007/978-3-642-20699-3_11
[5]   ANTIOXIDANT ACTIVITY OF SOME DIARYLSELENIDES IN BIOLOGICAL-SYSTEMS [J].
ANDERSSON, CM ;
HALLBERG, A ;
LINDEN, M ;
BRATTSAND, R ;
MOLDEUS, P ;
COTGREAVE, I .
FREE RADICAL BIOLOGY AND MEDICINE, 1994, 16 (01) :17-28
[6]   Proteolytic clipping of histone tails: the emerging role of histone proteases in regulation of various biological processes [J].
Azad, Gajendra Kumar ;
Tomar, Raghuvir S. .
MOLECULAR BIOLOGY REPORTS, 2014, 41 (05) :2717-2730
[7]   A Solvent- and Metal-Free Synthesis of 3-Chacogenyl-indoles Employing DMSO/I2 as an Eco-friendly Catalytic Oxidation System [J].
Azeredo, Juliano B. ;
Godoi, Marcelo ;
Martins, Guilherme M. ;
Silveira, Claudio C. ;
Braga, Antonio L. .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09) :4125-4130
[8]   Oxidations Catalyzed By Seleninic Acids and Anhydrides, Their Precursors and Congeners [J].
Back, Thomas G. .
CURRENT GREEN CHEMISTRY, 2016, 3 (01) :76-91
[9]   In vitro antioxidant activity and in vivo antidepressant-like effect of α-(phenylselanyl) acetophenone in mice [J].
Barbieri Gerzson, Mariana Freire ;
Victoria, Francine N. ;
Radatz, Catia S. ;
de Gomes, Marcelo G. ;
Boeira, Silvana P. ;
Jacob, Raquel G. ;
Alves, Diego ;
Jesse, Cristiano Ricardo ;
Savegnago, Lucielli .
PHARMACOLOGY BIOCHEMISTRY AND BEHAVIOR, 2012, 102 (01) :21-29
[10]   STUDIES ON THE REACTION OF PRIMARY AND SECONDARY-AMINES WITH PHENYLSELENINIC ANHYDRIDE AND WITH PHENYLSELENINIC ACID [J].
BARTON, DHR ;
LUSINCHI, X ;
MILLIET, P .
TETRAHEDRON, 1985, 41 (21) :4727-4738