4.5 Article

Construction of Pyrrolocoumarin Cores through Double C-H Annulation Cascade

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2022, Issue 22, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202200550

Keywords

Annulation; C-C coupling; C-H activation; Homogeneous catalysis; Rhodium

Funding

  1. JSPS KAKENHI [JP18H04627, 20H02745, 18K19083]
  2. Grants-in-Aid for Scientific Research [20H02745, 18K19083] Funding Source: KAKEN

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A Rh(III)-catalyzed double C-H annulation of 3-(acetylamino)coumarins with internal arylacetylenes is reported, which selectively produces 8-aryl-6H- chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-ones accompanied by the formation of two C-C and two C-N bonds. This method also provides a straightforward route to natural product inspired pentacyclic pyrrolocoumarin derivatives from readily available building blocks.
Rhodium(III)-catalyzed double C-H annulation of 3-(acetylamino)coumarins with internal arylacetylenes is reported. The reaction proceeds smoothly accompanied by two C-C and two C-N bond formation to produce 8-aryl-6H- chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-ones selectively. It also provides a straightforward route to natural product inspired pentacyclic pyrrolocoumarin derivatives from readily available building blocks.

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