4.4 Article

A convenient access to furo[3,2-c]pyridin-6(5H)-ones by the reaction of 5-iodo-4-methoxy-2-pyridones with terminal alkynes under microwave-enhanced Sonogashira conditions

Journal

TETRAHEDRON LETTERS
Volume 50, Issue 26, Pages 3299-3301

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.02.073

Keywords

Sonogashira cross-coupling; Alkynes; Annulation; Furopyridinones; Microwave-assisted synthesis

Funding

  1. Bayer CropScience
  2. CNRS
  3. French Ministry of Higher Education and Research (MESR)

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N-Alkyl-3-aryl-5-iodo-4-methoxypyridin-2(1H)-ones readily undergo sequential acetylide cross-coupling, demethylation, and furan annulation under classical Sonogashira reaction conditions to furnish 7-arylfuro[3,2-c]pyridin-4(5H)-ones, a class of hitherto unknown compounds, in a one-pot operation. Microwave irradiation was found to significantly reduce reaction times and to allow lower catalysts and reagent loadings. (C) 2009 Elsevier Ltd. All rights reserved.

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