4.5 Article

Palladium-Catalyzed Reaction of MBH Acetates and Terminal Alkynes: Cascade Synthesis of Phenanthridine and 6-Arylethynylphenanthridine

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 31, Pages 4284-4295

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201800725

Keywords

Nitrogen heterocycles; Fused-ring systems; Palladium; Domino reactions; Alkynes

Funding

  1. University Grants Commission (UGC), New Delhi
  2. Council of Scientific and Industrial Research (CSIR), New Delhi
  3. Department of Science and Technology, New Delhi [EMR/2016/000706]

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We have described the palladium-catalyzed regioselective cascade synthesis of phenanthridines and 6-arylethynylphenanthridines in good to excellent yields from a reaction between Morita-Baylis-Hillman (MBH) acetates and terminal alkynes. These cascade reactions are temperature controlled and favor the formation of phenanthridines when conducted at 50 degrees C and of 6-arylethynylphenanthridines when performed at 80 degrees C.

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