4.7 Article

Ruthenium-Catalyzed Cycloisomerization of Aromatic Homo- and Bis-Homopropargylic Amines/Amides: Formation of Indoles, Dihydroisoquinolines and Dihydroquinolines

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 11-12, Pages 1933-1937

Publisher

WILEY-BLACKWELL
DOI: 10.1002/adsc.201100095

Keywords

alkynylamines; azaheterocycles; cycloisomerization; ruthenium; vinylidenes

Funding

  1. MICINN (Spain) [CTQ2008-06557]
  2. Consolider Ingenio [CSD2007-00006]
  3. Xunta de Galicia
  4. European Regional Development Fund [2007/XA084, INCI-TE08PXIB209024PR]
  5. USC

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Ruthenium-catalyzed cycloisomerizations of aromatic homo- and bis-homopropargylic amines/amides efficiently afford indoles, dihydroisoquinolines and dihydroquinolines. These processes were regioselective (5- and 6-endo cyclizations) on using key Ru vinylidene intermediates. The presence of an amine/ammonium base-acid pair increased the rate of cyclization and facilitated the catalytic turnover.

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