N-Cinnamoyl-9-aminoanthracenes cyclise with PPA or triflic acid to form novel 2-azahexacyclo[10.6.6.01,5.06,11.013,18.019,24]tetracosa-6(11),7,9,13,15,17,19(24),20,22-nonaen-3-ones. In contrast, both N-cinnamoyl-N-methyl-9-(2-aminomethyl)anthracene and N-cinnamoyl-9-(2-aminoethyl)anthracene undergo an intramolecular Diels–Alder cycloaddition.
F. D. King, A. Aliev, S. Caddick and D. Tocher, Org. Biomol. Chem., 2014, 12, 3211 DOI: 10.1039/C4OB00411F
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