Synthesis of novel heteroaromatics structurally related to ellipticine alkaloids via thermolysis of pyridannulated enyne-carbodiimides.
New synthetic pathways to the 5H-pyrido[3',4':4,5]pyrrolo[2,3-b]quinolines 6, the 6H-pyrido[3',4':4,5]pyrrolo[2,3-b][1,6]naphthyridines 7, and the 11H-pyrido[4',3':4,5]pyrrolo[2,3-b]quinolines 8 via thermolysis of the pyridannulated enyne-carbodiimides 14, 19, and 23 were established. These novel heteroaromatic systems are structurally related to ellipticine alkaloids and could serve as DNA-intercalating agents.
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506-6045, USA.
Xiaoling
X
Lu
Jeffrey L
JL
Petersen
Kung K
KK
Wang
D000470:Alkaloids / Q000138:chemical synthesis*; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D018360:Crystallography, X-Ray; D004611:Ellipticines / Q000138:chemical synthesis*; D015394:Molecular Structure; D009287:Naphthyridines / Q000138:chemical synthesis*; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis*; D011725:Pyridines / Q000138:chemical synthesis*; D011804:Quinolines / Q000138:chemical synthesis*
D000470:Alkaloids; D000970:Antineoplastic Agents; D004611:Ellipticines; D009287:Naphthyridines; D011084:Polycyclic Aromatic Hydrocarbons; D011725:Pyridines; D011804:Quinolines