ChemInform Abstract: Synthesis of Benzo[f]quinoline Derivatives by Condensation of Arylmethylene‐2‐naphthylamines with Ethyl Acetoacetate.

Козлов, Н. Г.; Sauts, R. D.; Gusak, K. N.

doi:10.1002/chin.200051138

Cited by 2 publications

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“…The papers [35][36][37][38] dealt with study of the catalytic condensation of azomethines of the 2-naphthylamine series with β-keto esters, opening up the way to the production of substituted carboxyl derivatives of benzo[f]quinoline with a high potential for biological activity. Acetoacetic ester and the ethyl esters of 2-furyl-, 2-quinolyl-, and 3-pyridyl-β-oxo carboxylic acids were brought into reaction with arylmethylidene-2-naphthylamines.…”

Section: Condensation Of Arylmethylidene-2-naphthylamines With the Esmentioning

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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Section: Condensation Of Arylmethylidene-2-naphthylamines With the Esmentioning

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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“…We formerly [1][2][3][4] demonstrated that the reaction of 6-aminoquinoline with aromatic aldehydes and methyl or methylene ketones (СН-acids) led to the formation of 4,7-phenanthrolines of versatile structures. In the series of СН-acids the most effi cient synthons are cyclic 1,3-diketones [3,4].…”

mentioning

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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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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ChemInform Abstract: Synthesis of Benzo[f]quinoline Derivatives by Condensation of Arylmethylene‐2‐naphthylamines with Ethyl Acetoacetate.

Cited by 2 publications

References 0 publications

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

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

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

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