N-肉桂酰基-9-氨基蒽的环化反应

Cyclisation reactions of N-cinnamoyl-9-aminoanthracenes.

作者信息

King Frank D, Aliev Abil, Caddick Stephen, Tocher Derek

机构信息

Department of Chemistry, University College London, 20 Gordon Street, London, UK.

出版信息

Org Biomol Chem. 2014 May 28;12(20):3211-21. doi: 10.1039/c4ob00411f. Epub 2014 Apr 11.

DOI:10.1039/c4ob00411f

PMID:24722646

Abstract

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.

摘要

N-肉桂酰基-9-氨基蒽与多聚磷酸（PPA）或三氟甲磺酸发生环化反应，形成新型的2-氮杂六环[10.6.6.0(1,5).0(6,11).0(13,18).0(19,24)]二十四碳-6(11),7,9,13,15,17,19(24),20,22-壬烯-3-酮。相比之下，N-肉桂酰基-N-甲基-9-(2-氨甲基)蒽和N-肉桂酰基-9-(2-氨乙基)蒽都发生分子内狄尔斯-阿尔德环加成反应。