A. B. Tereshko

1,3-Cyclohexanedione in the Synthesis of Fused Derivatives of 4,7-Phenanthroline

Abstract12-Aryl(heteryl,cyclohexenyl)-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-ones were synthesized by condensation of 1,3-cyclohexanedione with 6-quinolylamine and aldehydes of aromatic, heterocyclic, and cyclohexene series.

Oxidation of 4,7-phenanthroline derivatives

Oxidation of 1,3-diphenyl-4,7-phenanthroline with potassium permanganate in alkaline medium results in transformation of the 4,7-phenanthroline ring system into 1,8-diaazafluorenone. Oxidation of 12-aryl-and 12-aryl-9,9-dimethyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-ones (condensation products of 6-arylmethylene-aminoquinolines with 1,3-cyclohexanedione and dimedone) with sodium nitrite in acetic acid leads to 12-aryl-9,10-dihydro-8H-benzo[b][4,7]phenanthrolin-11-ones. 13-Aryl-7,13-dihydro-12H-indeno-[2,1-b][4,7]phenanthrolin-12-ones obtained by reaction of 6-arylmethyleneaminoquinolines with 1,3-indandione are oxidized to 13-aryl-12H-indeno[2,1-b][4,7]phenanthrolin-12-ones on heating in nitrobenzene.

Vanillin esters of aromatic carboxylic acids in the synthesis of benzo[a]acridine and benzo[b][4,7]phenanthroline derivatives

By condensation of vanillin esters of substituted benzoic acids with 2-naphthylamine and 6-quinolylamines and also with cyclic β-diketones (1,3-cyclohexanedione and dimedone) 2-methoxy-4-(11-oxo-7,8,9,10,11,12-hexahydrobenzo[a]acridin-12-yl)-and 2-methoxy-4-(11-oxo-7,8,9,10,11,12-hexahydrobenzo[b][4,7]-phenanthrolin-12-yl)phenyl benzoates were prepared.

Synthesis of Fused Derivatives of 4,7-Phenanthroline by Condensation of 6-Aminoquinoline with Aromatic Aldehydes and Dimedone

Abstract8-Aryl-11,11-dimethyl-7,8,9,10,11,12-hexahydrobenzo[a]phenanthrolin-9-ones were obtained by condensation of 6-aminoquinoline with aromatic aldehydes and dimedone.

Vanillin Esters of Aliphatic Acids in the Synthesis of 4,7-Phenanthroline Derivatives

Condensation of vanillin esters of aliphatic acids with 6-aminoquinoline and cyclic c-diketones (1,3-cyclohexanedione and dimedone) afforded new 2-methoxy-4-(11-oxo-7,8,9,10,11,12-hexahydrobenzo[b][4,7]phenanthrolin-12-yl)phenyl esters of carboxylic acids.

Condensation of quinolin-5-amine with aromatic aldehydes and cyclohexane-1,3-dione

Abstract7-Aryl(hetaryl, cyclohexenyl)-7,10,11,12-tetrahydrobenzo[b][1,7]phenanthrolin-8(9H)-ones were synthesized by three-component condensation of aromatic and heteroaromatic aldehydes and cyclohex-3-ene-1-carbaldehyde with quinolin-5-amine and cyclohexane-1,3-diones.

Phendione in the Synthesis of Annelated Derivatives of 4,7-Phenanthroline

By condensation of 5-phenyl-1,3-cyclohexanedione with 6-quinolylamine and aldehydes of aromatic, heterocyclic, and cyclohexene series new 12-aryl(heteryl, cyclohexenyl)-9-phenyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-ones were prepared. The presence of diastereomers in the target reaction products was determined by 1H NMR spectroscopy.

Synthesis of 4,7-phenanthroline methyl derivatives

Abstract6-Aminoquinaldine condensation with aromatic aldehydes and cyclic β-diketones (1,3-cyclohexanedione or dimedone) in butanol afforded new 12-aryl-3-methyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-ones and their 9,9-dimethyl derivatives.

Barbituric acid in the synthesis of fused 1,7-phenanthroline derivatives

New 7-aryl(hetaryl)-7,8,9,10,11,12-hexahydropyrimido[5,4-b][1,7]phenanthroline-9,11-diones have been synthesized by three-component condensation of barbituric acid with quinolin-5-amine and aromatic or heteroaromatic aldehydes.

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

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).