Phendione and anisylhydroresorcinol in the synthesis of 1,7-phenanthroline derivatives

Козлов, Н. Г.; Tereshko, A. B.; Королева, Е. В.; Ignatovich, Zh. B.; Gusak, K. N.

doi:10.1134/s1070428009020183

Cited by 6 publications

(4 citation statements)

References 5 publications

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“…The structure of regioisomers with the 10-methoxycarbonyl group was assigned basing on the comparison of their spectra with those of 6-amineоquinoline analogs. The chemical shifts and the geminal coupling constant for the protons of the methylene group were close to the corresponding values in the spectra of 10-methoxycarbonyl regioisomer described before [10].…”

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confidence: 76%

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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

Козлов

Tereshko

2011

Russ J Org Chem

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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 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 regiospecifi cally 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). Isomers ratio (IVа):(Vа) ~73 : 27. 1 Н NMR spectrum, δ, ppm (IVа): 2.10 s (3Н, ArCH 3 ), 2.73 d.d (1Н, Н 8е , 2 J 8е,8а 17.0, 3 J 8е,9а 4.5 Hz), 2.94 d.d (1Н, Н 8а , 2 J 8а,8е 17.0, 3 J 8а,9a 12.0 Hz), 3.03 d.t (1Н, Н 9 , 3 J 9а,8a 12.0, 3 J 9а,10a 12.0, 3 s (NH). Found (isomers mixture ), %: С 73.93; Н 4.91; N 5.26. 11-oxo-7,8,9,10,11,12-hexahydrobenzo[b][4,7]phenanthroline-10-carboxylate [10,12-trans-(IVo) and 10,12-cis-(Vo)]. Yield of isomers mixture 75%. Isomers ratio (IVo) : (Vo) ~ 69 : 31. 1 Н NMR spectrum, δ, ppm (IVo): 2.73 d.d (1Н, Н 8е , 2 J 8е,8а 17.0, 3 J 8е,9а 4.5 Hz ), 2.92 d.d (1Н, Н 8а , 2 J 8а,8е 17.0, 3 J 8а,9a 12.0 Hz), 3.05 d.t (1Н, Н 9 , 3 J 9а,8a 12.0, 3 J 9а,10a 12.0, 3 J 9а,8е 4.5 Hz), 3.45 s (3Н, ОCH 3 ), 3.92 d (1Н, Н 10 , 3 J 10а,9a 12.0 Hz), 4.95 s (2Н, ОСН 2 Methyl 9-(benzo[d][1,3]dioxol-5-yl)-12-(4-benzyloxyphenyl)-

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confidence: 76%

“…Three-component condensation of compounds I, II, and aldehydes IIIа-IIIs [10]. Equimolar quantities (5 mmol each) of methyl 2-(benzo[d] [1,3]dioxol-5-yl)-4,6-dioxocyclohexanecarboxylate (I), 6-aminoquinoline (II), and aldehyde IIIа-IIIs in 15 ml of 1-butanol was boiled till the completion of the reaction (GLC monitoring, ~2-3 h).…”

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confidence: 99%

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

Козлов

Tereshko

2011

Russ J Org Chem

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“…The strong bands at 3260 and 1630 cm -1 correspond respectively to the stetching and bending vibrations of the secondary amino group. The stretching vibrations of alkyl groups and cycloaliphatic C-H bonds give rise to the bands in the region 2960-2870 cm - of the protons of the methylene group at C 8 are close to those of the regioisomeric 10-methoxycarboxylate published before [9].…”

mentioning

confidence: 79%

Synthesis of methyl 9-mesityl-12-aryl-11-oxo-7,8,9,10,11,12-hexahydrobenzo[a]- acridine-10-carboxylates

Козлов

2011

Russ J Org Chem

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“…Preparative methods were proposed, and new derivatives of benzo[f ]quinoline, benzo[a]acridine, and 1,7-and 4,7-phenanthroline (46 and 47 respectively) were synthesized (Scheme 16) as prospective luminophores, light-sensitive materials, and bioactive substances with a broad range of activity. It was found that if 5-monosubstituted 1,3-cyclohexanediones [5-Ph-, 5-Me-, 5-(4-MeOC 6 Н 4 )-, 5-(4-BuOC 6 Н 4 )-, 5-(2-furyl)] containing an asymmetric center were used, the condensation products were formed as mixtures of two diastereomers [77][78][79][80].…”

Section: Condensation Of Naphthyl-and Quinolylamines With Aromatic Almentioning

confidence: 99%

Development of the catalytic synthesis of compounds of the quinoline series (the N. S. Kozlov reaction) (Review)*

Козлов¹,

Gusak²,

Kadutskii³

2010

Chem Heterocycl Comp

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Phendione and anisylhydroresorcinol in the synthesis of 1,7-phenanthroline derivatives

Cited by 6 publications

References 5 publications

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

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

Synthesis of methyl 9-mesityl-12-aryl-11-oxo-7,8,9,10,11,12-hexahydrobenzo[a]- acridine-10-carboxylates

Development of the catalytic synthesis of compounds of the quinoline series (the N. S. Kozlov reaction) (Review)*

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