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2011•Russian Journal of Organic ChemistryRequires access

Synthesis of methyl 9-(benzo[d][1,3]dioxol-5-yl)-12-aryl(heteryl, cyclohexenyl)-11-oxo-7,8,9,10,11,12-hexahydrobenzo[b][4,7]phenanthroline-10-carboxylates

Н. Г. Козлов, A. B. Tereshko

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Abstract

By condensation of 6-aminoquinoline with methyl 2-(benzo[ d ][1,3]dioxol-5-yl)-4,6-dioxocyclohexanecarboxylate and aldehydes of aromatic, heteroaromatic, and cyclohexene series new 4,7-phenanthroline derivatives were synthesized. The reaction performed in 1-butanol proceeded regiospecifically and with a moderate degree of stereoselectivity resulting in a mixture of cis - and trans -methyl 9-(benzo-[ d ][1,3] dioxol-5-yl)-12-aryl(heteryl, cyclohexenyl)-11-oxo-7,8,9,10,11,12-hexahydrobenzo-[ b ][4,7]-phenanthroline-10-carboxylates (∼30: 70).

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What this paper is about

By condensation of 6-aminoquinoline with methyl 2-(benzo[ d ][1,3]dioxol-5-yl)-4,6-dioxocyclohexanecarboxylate and aldehydes of aromatic, heteroaromatic, and cyclohexene series new 4,7-phenanthroline derivatives were synthesized. The reaction performed in 1-butanol proceeded regiospecifically and with a moderate degree of stereoselectivity resulting in a mixture of cis - and trans -methyl 9-(benzo-[ d ][1,3] dioxol-5-yl)-12-aryl(heteryl, cyclohexenyl)-11-oxo-7,8,9,10,11,12-hexahydrobenzo-[ b ][4,7]-phenanthroline-10-carboxylates (∼30: 70).

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Available abstract

By condensation of 6-aminoquinoline with methyl 2-(benzo[ d ][1,3]dioxol-5-yl)-4,6-dioxocyclohexanecarboxylate and aldehydes of aromatic, heteroaromatic, and cyclohexene series new 4,7-phenanthroline derivatives were synthesized. The reaction performed in 1-butanol proceeded regiospecifically and with a moderate degree of stereoselectivity resulting in a mixture of cis - and trans -methyl 9-(benzo-[ d ][1,3] dioxol-5-yl)-12-aryl(heteryl, cyclohexenyl)-11-oxo-7,8,9,10,11,12-hexahydrobenzo-[ b ][4,7]-phenanthroline-10-carboxylates (∼30: 70).

Key concepts: Chemistry, Phenanthroline, Condensation, Aryl, Medicinal chemistry, Cyclohexene, Stereoselectivity, Condensation reaction

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Synthesis of methyl 9-(benzo[d][1,3]dioxol-5-yl)-12-aryl(heteryl, cyclohexenyl)-11-oxo-7,8,9,10,11,12-hexahydrobenzo[b][4,7]phenanthroline-10-carboxylates — Research Paper | ScholarLens