Isonitrile trapping reactions under thermolysis of alkoxyamines for the synthesis of quinolines

Organic Letters
Birgit Janza, Armido Studer

Abstract

[reaction: see text] An efficient tandem radical process comprising a thermal alkoxyamine homolysis, an isonitrile trapping reaction, a 5-exo-trig cyclization, and a homolytic aromatic substitution leads to substituted dihydroquinolines. Depending on the substituent R(1), oxidation to dihydro-1H-cyclopenta[b]quinolines (for R(1) = aryl) or tautomerization to tetrahydro-1H-cyclopenta[b]quinolines (for R(1) = CO(2)Me, CN) occurs. The heterocycles are obtained in moderate to good yields. Upon using microwave-induced heating, the reaction time can be shortened from 3 days to 30 min.

References

Apr 27, 2001·Chemistry : a European Journal·A Studer
Jan 23, 2004·Chemical Communications : Chem Comm·Christian Wetter, Armido Studer
Nov 24, 2004·Angewandte Chemie·C Oliver Kappe

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Citations

Nov 28, 2013·Organic Letters·Dirk LeifertArmido Studer
Feb 6, 2014·Organic Letters·Bo Zhang, Armido Studer
Aug 30, 2012·The Journal of Organic Chemistry·San Khong, Ohyun Kwon
Oct 26, 2016·Angewandte Chemie·Yajun Li, Fraser F Fleming
May 13, 2014·Chemical Communications : Chem Comm·Gérard AudranSylvain R A Marque
Feb 13, 2016·Organic & Biomolecular Chemistry·Jian LeiQiang Zhu
Apr 12, 2016·Chemical Communications : Chem Comm·Dirk LeifertArmido Studer
Dec 17, 2014·Chemistry : a European Journal·Sigrid HolleManuel Alcarazo
May 4, 2011·Angewandte Chemie·Ludger Tebben, Armido Studer
May 23, 2019·Angewandte Chemie·Dirk Leifert, Armido Studer
Jul 7, 2011·Chemistry : a European Journal·Hendrik WagnerArmido Studer
Oct 31, 2014·Organic & Biomolecular Chemistry·Bo Zhang, Armido Studer
Aug 27, 2009·The Journal of Organic Chemistry·Mark J Thompson, Beining Chen
May 9, 2009·Organic Letters·Inga C WienhöferIlhyong Ryu
Dec 10, 2016·Organic Letters·Ludovik Noël-DuchesneauSami Lakhdar
Oct 3, 2018·Journal of the American Chemical Society·Gabriel Dos Passos GomesIgor V Alabugin

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