4.4 Article

Formal [4+2] cycloaddition of quinolines, pyridines, and isoquinolines with 3-ethoxycyclobutanones

Journal

TETRAHEDRON LETTERS
Volume 57, Issue 27-28, Pages 3050-3052

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2016.06.011

Keywords

Cyclobutanone; [4+2] cycloaddition; Quinoline; Pyridine; Isoquinoline

Funding

  1. JSPS KAKENHI Grant [15K07855]
  2. Grants-in-Aid for Scientific Research [15K07855] Funding Source: KAKEN

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3-Ethoxycyclobutanones reacted with pyridines, quinolines, and isoquinolines to give the corresponding formal [4+2] cycloadducts, 9a-hydro-2H-quinolizin-2-one derivatives, by using Me3SiOTf in acetonitrile. Cycloaddition of 3-ethoxy-2-monoalkylcyclobutanones to 5-nitroquinoline or 4-cyanopyridine proceeded stereoselectively. (C) 2016 Elsevier Ltd. All rights reserved.

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