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.
Tu
Shanghui
S
Department of Chemistry, Capital Normal University, 100048, Beijing, China.
Ding
Chunyong
C
Hu
Wenxiang
W
Li
Fulong
F
Yao
Qizheng
Q
Zhang
Ao
A
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