Synthesis of Biologically Active Indenoisoquinoline Derivatives via a One-Pot Copper(II)-Catalyzed Tandem Reaction.
A concise route for the synthesis of indenoisoquinoline derivatives from 2-iodobenzamide and 1,3-indanedione derivatives in the presence of copper(II) chloride and cesium carbonate in acetonitrile solvent is reported. A wide variety of 2-iodobenzamide derivatives and indandiones could be used to synthesize indenoisoquinoline derivatives and other fused indenoisoquinoline in moderate to good yields. This methodology was adapted for the one-step synthesis of a series of clinically active topoisomerase I inhibitors such as NSC 314622, LMP-400, LMP-776.
Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Ting-Chow Road, Taipei 116, Taiwan R.O.C.
Chia-Yu
CY
Huang
Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Ting-Chow Road, Taipei 116, Taiwan R.O.C.
Veerababurao
V
Kavala
Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Ting-Chow Road, Taipei 116, Taiwan R.O.C.
Chun-Wei
CW
Kuo
Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Ting-Chow Road, Taipei 116, Taiwan R.O.C.
Ashok
A
Konala
Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Ting-Chow Road, Taipei 116, Taiwan R.O.C.
Tang-Hao
TH
Yang
Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Ting-Chow Road, Taipei 116, Taiwan R.O.C.
Ching-Fa
0000-0002-8692-5156
CF
Yao
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure
D007192:Indenes; D007546:Isoquinolines; C093581:indene; D003300:Copper; C039109:isoquinoline