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Direct Synthesis of Perylene‐Fused Cyclic Ketones from Perylene and 2‐Alkenoic Acids
Author(s) -
Głodek Marta,
Makal Anna,
Kłys Arkadiusz,
Zakrzewski Janusz,
Plażuk Damian
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600661
Subject(s) - perylene , chemistry , friedel–crafts reaction , acylation , catalysis , yield (engineering) , alkylation , organic chemistry , intramolecular force , medicinal chemistry , molecule , materials science , metallurgy
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‐4 H ‐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‐1 H ‐benzo[ cd ]perylen‐1‐one.