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Issue 36, 2015
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Synthesis of quinoxalines or quinolin-8-amines from N-propargyl aniline derivatives employing tin and indium chlorides

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Abstract

Pyrazino compounds such as quinoxalines are 1,4-diazines with widespread occurrence in nature. Quinolin-8-amines are isomerically related and valuable scaffolds in organic synthesis. Herein, we present intramolecular main group metal Lewis acid catalyzed formal hydroamination as well as hydroarylation methodology using mono-propargylated aromatic ortho-diamines. The annulations can be conducted utilizing equal aerobic conditions with either stannic chloride or indium(III) chloride and represent primary examples for main group metal catalyzed 6-exo-dig and 6-endo-dig, respectively, cyclizations in such settings. Both types of reactions can also be utilized in a one-pot manner starting from ortho-nitro N-propargyl anilines using stoichiometric amounts SnCl2·2H2O or In powder. Mechanistic considerations are presented regarding the substituent-depending regioselectivity.

Graphical abstract: Synthesis of quinoxalines or quinolin-8-amines from N-propargyl aniline derivatives employing tin and indium chlorides

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Publication details

The article was received on 24 Jul 2015, accepted on 12 Aug 2015 and first published on 12 Aug 2015


Article type: Paper
DOI: 10.1039/C5OB01532D
Citation: Org. Biomol. Chem., 2015,13, 9373-9380
  • Open access: Creative Commons BY-NC license
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    Synthesis of quinoxalines or quinolin-8-amines from N-propargyl aniline derivatives employing tin and indium chlorides

    S. Aichhorn, M. Himmelsbach and W. Schöfberger, Org. Biomol. Chem., 2015, 13, 9373
    DOI: 10.1039/C5OB01532D

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