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Quino[1,2‐ c ]quinazolines. I. Synthesis of quino[1,2‐ c ]quinazolinium derivatives and the related indazolo[2,3‐ a ]quinoline derivatives as analogs of the antitumor benzo[ c ]phenanthridine alkaloids

1980; Wiley; Volume: 17; Issue: 7 Linguagem: Inglês

10.1002/jhet.5570170726

1943-5193

Steven Phillips, Raymond N. Castle,

Synthesis and Biological Evaluation

Abstract 9,10‐Dimethoxy‐1,2,3,4,12,13‐hexahydro‐1‐oxoquino[1,2‐ c ]quinazolinium perchlorate, 1,2,3,4,13,24‐hexahydro‐1‐oxo[1,3]dioxolo[4,5‐ g ]quino[1,2‐ c ]quinazolinium perchlorate, 6‐methyl‐2,3,9,10‐tetramethoxyquino‐[1,2‐ c ]quinazolinium perchlorate and 2,3‐dimethoxy‐13‐methyl[1,3]dioxolo[4′,5′:6,7]quino[1,2‐ c ]quinazolinium perchlorate were synthesized as analogs of the potent antitumor benzo[ c ]phenanthridine alkaloids nitidine and fagaronine. The related 2,3,8,9‐tetramethoxyindazolo[2,3‐ a ]quinoline and 2,3‐dimethoxy[1,3]dioxolo‐[4,5‐ g ]indazolo[2,3‐ a ]quinoline were also synthesized. Further, the novel formation of 6,7‐dimethoxy‐2‐(2‐ethylamino‐4,5‐dimethoxyphenyl)quinoline via reductive alkylation with Raney nickel in refluxing ethanol is also reported.