Cyclisation reactions of N-cinnamoyl-9-aminoanthracenes.
N-Cinnamoyl-9-aminoanthracenes cyclise with PPA or triflic acid to form novel 2-azahexacyclo[10.6.6.0(1,5).0(6,11).0(13,18).0(19,24)]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.
Department of Chemistry, University College London, 20 Gordon Street, London, UK. fd.king@btinternet.com.
Frank D
FD
King
Abil
A
Aliev
Stephen
S
Caddick
Derek
D
Tocher
D000143:Acids / Q000737:chemistry; D000873:Anthracenes / Q000138:chemical synthesis* / Q000737:chemistry; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D008968:Molecular Conformation; D066244:Proton Magnetic Resonance Spectroscopy; D011789:Quantum Theory
D000143:Acids; D000873:Anthracenes