Facile synthesis of indole- or benzofuran-fused benzo[a]carbazole-1,4-diones using a tandem two-step reaction sequence.
An efficient three-step approach was developed to assemble indole- or benzofuran-fused benzocarbazole-1,4-diones in 42-53% overall yield. This approach includes AgOAc-promoted oxidative cyclization of 2,6-di-bromocyclohexene-1,4-dione with indol-3-ylpropanoid acid, condensation of the resulting bromocarbazole intermediates with phenols or anilines, followed by Pd(OAc)-catalyzed cyclization. Such convenient synthetic protocol and the novelty of the corresponding products will largely assist our drug design and development program.
Department of Chemistry, Capital Normal University, 100048, Beijing, China.
Shanghui
S
Tu
Chunyong
C
Ding
Wenxiang
W
Hu
Fulong
F
Li
Qizheng
Q
Yao
Ao
A
Zhang
D001572:Benzofurans / Q000737:chemistry*; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000737:chemistry*
D001572:Benzofurans; D002227:Carbazoles; D007211:Indoles; C041514:carbazole; C105430:benzofuran