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Synthesis 2022; 54(12): 2894-2806
DOI: 10.1055/s-0037-1610793
DOI: 10.1055/s-0037-1610793
paper
Pd-Catalyzed N–H or C–H Functionalization/Oxidative Cyclization for the Efficient Synthesis of N-Aryl-Substituted [3,4]-Fused Pyrrolocoumarins
Abstract
1-Aryl-2-methyl- or 3-methylchromeno[4,3-b]pyrrol-4(1H)-ones have been synthesized in excellent yields by the Pd-catalyzed intramolecular aza-Wacker-type cyclization of 3-allyl-4-arylaminocoumarins or C–H insertion/oxidative cyclization of N-allyl-N-aryl-4-aminocoumarins, respectively, in the presence of Cu(OAc)2 in acetic acid under heating. The starting allylcoumarins have been prepared by the allylation of 4-arylaminocoumarins with allyl bromide in CH3CN in the presence of Cs2CO3 at room temperature. Preliminary biological tests indicated interesting antioxidant activity and significant levels of inhibition of soybean lipoxygenase.
Key words
[3,4]-fused pyrrolocoumarins - Pd-catalyzed aza-Wacker oxidative cyclization - copper acetate - 3-allyl-4-arylaminocoumarins - N-allyl-N-aryl-4-aminocoumarinsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610793.
- Supporting Information
Publication History
Received: 20 December 2021
Accepted after revision: 24 January 2022
Article published online:
09 March 2022
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For a review see:
Selected examples for the synthesis of ningalin B:
Pd-Catalyzed synthesis of pyrroles:
Selective examples for the Pd-catalyzed synthesis of indoles:
Selective examples for the intramolecular aza-Wacker reaction: