SeCl2 -Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes

The Journal of Organic Chemistry
Guilherme M MartinsClaudio C Silveira

Abstract

A novel and efficient SeCl2-mediated chalcogenative cyclization strategy toward 3-selenophen-3-yl-1 H-indoles from readily available and conveniently substituted propargyl indoles is described. It entails an unprecedented selenirenium-induced 1,2-indolyl shift prompted by the electrophilic addition of SeCl2 to the triple bond of the propargyl indole, followed by cyclization through the intermediacy of a 1-seleno-1,3-diene. The reaction takes place at room temperature and shows excellent selectivity, broad substrate scope, and wide functional group tolerance.

References

Jun 5, 2004·The Journal of Organic Chemistry·Alan R KatritzkyKostyantyn Kirichenko
May 26, 2007·Angewandte Chemie·Alexander S Dudnik, Vladimir Gevorgyan
Dec 1, 2007·Chemical Communications : Chem Comm·Martin HeeneySteve Tierney
Jan 5, 2008·Journal of the American Chemical Society·Alexander S DudnikVladimir Gevorgyan
Mar 5, 2008·Chemistry : a European Journal·Benedikt Crone, Stefan F Kirsch
May 7, 2008·Journal of the American Chemical Society·Asit PatraMichael Bendikov
Jun 23, 2009·Pharmacology, Biochemistry, and Behavior·Ethel A WilhelmLucielli Savegnago
Nov 26, 2009·Journal of Medicinal Chemistry·Petr NausMichal Hocek
Apr 17, 2010·Cell Biology and Toxicology·Ethel Antunes WilhelmCristina Wayne Nogueira
Aug 3, 2010·Bioorganic & Medicinal Chemistry Letters·Pao-Chiung HongChu-Bin Liao
Jan 7, 2011·Organic & Biomolecular Chemistry·Cristiano R B Rhoden, Gilson Zeni
Mar 30, 2011·Journal of Medicinal Chemistry·Jason A WilesMilind Deshpande
Jul 21, 2011·Beilstein Journal of Organic Chemistry·David Garayalde, Cristina Nevado
Dec 1, 2003·Environmental Toxicology and Pharmacology·Flavia C MeottiCristina W Nogueira
Aug 2, 2011·Beilstein Journal of Organic Chemistry·Estela AlvarezRoberto Sanz
May 26, 2012·Mini Reviews in Medicinal Chemistry·Nasir Ali Shafakat AliMazahar Farooqui
Feb 28, 2013·Organic Letters·Vutukuri Prakash ReddyNobuaki Kambe
Apr 3, 2014·Chembiochem : a European Journal of Chemical Biology·Daniela MilbredtKarl-Heinz van Pée
Oct 6, 2014·European Journal of Medicinal Chemistry·Pavel ArsenyanIrina Shestakova
Nov 11, 2014·Beilstein Journal of Organic Chemistry·Laura G SarbuLucian M Birsa
Sep 23, 2011·Tetrahedron·Douglass F Taber, Pavan K Tirunahari
Apr 23, 2015·Organic & Biomolecular Chemistry·Damiano TaniniMarco d'Ischia
Jul 28, 2015·Chemistry : a European Journal·Estela ÁlvarezRoberto Sanz
Sep 22, 2015·Journal of the American Chemical Society·Jitan ZhangYuhong Zhang
Nov 10, 2015·Archiv der Pharmazie·Lucie HellerRené Csuk
Nov 22, 2015·The Journal of Organic Chemistry·Kayla M Fisher, Yuri Bolshan

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Citations

Dec 17, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Paola S HellwigEder J Lenardão
Mar 16, 2021·Journal of the American Chemical Society·Ayan DasguptaRebecca L Melen

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