Direct Synthesis of Perylene-Fused Cyclic Ketones from Perylene and 2-Alkenoic Acids

作者:Glodek Marta; Makal Anna; Klys Arkadiusz; Zakrzewski Janusz; Plazuk Damian
来源:European Journal of Organic Chemistry, 2016, 2016(24): 4215-4223.
DOI:10.1002/ejoc.201600661

摘要

An efficient, one-pot methodology of direct synthesis of perylene-fused cyclic ketones from perylene and 2-alkenoic acids under acidic catalytic conditions has been developed. The reaction of perylene with 2,3-disubstituted 2-alkenoic acid leads, via Friedel-Crafts acylation followed by Nazarov cyclization, to the formation of disubstituted 5,6-dihydro-4H-cyclopenta[b]perylen-4-ones in high yield (up to 97%) and high diastereoselectivity, whereas the reaction with acrylic acid leads, via alkylation followed by intramolecular Friedel-Crafts acylation, to 2,3-dihydro-1H-benzo[cd]perylen-1-one.

  • 出版日期2016-8

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