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

Козлов, Н. Г.; Tereshko, A. B.; Gusak, K. N.

doi:10.1134/s1070428002120199

Cited by 14 publications

(7 citation statements)

References 4 publications

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“…The reaction of 6‐aminoquinoline 204 with cyclohexane‐1,3‐diones and formaldehyde produces partially reduced pyrido[3,2‐ a ]acridinones 205 (R 2 = H, Scheme ) . Inclusion of an araldehyde in the reaction mixture, instead of the formaldehyde, produces corresponding products 205 (R 2 = Ar; 10 examples, 65–81 %) …”

Section: Pyrido[32‐a]acridine {Benzo[b][47]phenanthroline}mentioning

confidence: 99%

Pyridoacridines in the 21st Century

Joule

Álvarez

2019

Eur J Org Chem

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This minireview summarizes the work developed during this century with compounds containing the pyridoacridine scaffold in its different isomeric forms. The isolation of natural products, syntheses, bioactivities, chelation capacity, and other properties of compounds containing this framework are discussed. For reasons of length, only compounds containing a maximum of seven condensed rings have been considered, with a few exceptions.

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Section: Pyrido[32‐a]acridine {Benzo[b][47]phenanthroline}mentioning

confidence: 99%

Pyridoacridines in the 21st Century

Joule

Álvarez

2019

Eur J Org Chem

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“…Multicomponent condensation reactions have recently been discovered as good method for the synthesis of organic compounds . Dihydropyrimidones have attracted considerable interest because of their wide range of biological activities . Moreover, several natural marine alkaloids with interesting biological activities contain the dihydropyrimidine‐5‐caroxylate moiety .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Mechanistic Study of Triheterocyclic 4H‐Pyrimido[2,1‐b]benzothiazole derivatives, One‐Pot Three‐component Reaction under Solvent‐Free Conditions

Sahu

Sharma

et al. 2014

Journal of Heterocyclic Chem

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An efficient method has been developed for the preparation of 4H‐pyrimido[2,1‐b]benzothiazole derivatives by the condensation of aldehydes, β‐ketoester, and 2‐amino benzothiazole under solvent and solvent‐free conditions using various catalysts. The reaction uses benzothiazole as a new component, and good yield is obtained at 60–65°C under solvent‐free conditions. Atom economies, good yield, environmentally benign, and easy to work‐up are some of the important features of this protocol. The present study suggests that acetic acid and metal catalysts follow different mechanism. In acetic acid, 2‐amino benzothiazole reacts with benzaldehyde, and resultant intermediate reacts with ethyl acetoacetate to give final product, whereas in the presence of metal catalysts, 2‐amino benzothiazole first reacts with ethyl acetoacetate, and resultant intermediate reacts with benzaldehyde to give pyrimido[2,1‐b]benzothiazole.

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confidence: 99%

“…We previously showed [1][2][3][4] that quinolin-6-amine reacts with aromatic aldehydes and methyl or methylene ketones (CH acids) to give various 4,7-phenanthroline derivatives. It was also found that cyclic 1,3-diketones are the most efficient reagents among CH acids [3,4]. Partly hydrogenated oxo derivatives of benzo[b] [4,7]phenanthroline obtained as a result of the above reactions attract interest as analogs of natural alkaloids, enzyme inhibitors, bactericidal agents, and antibiotics [5][6][7][8].…”

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confidence: 99%

Synthesis of methyl 7-aryl(hetaryl, cyclohexenyl)-10,10-dimethyl-8-oxo-7,8,9,10,11,12-hexahydrobenzo[b][1,7]phenanthroline-9-carboxylates

Козлов

Tereshko

2010

Russ J Org Chem

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Three-component condensation of quinolin-5-amine with methyl 2,2-dimethyl-4,6-dioxocyclohexane-1-carboxylate and aromatic (heteroaromatic) aldehydes or cyclohex-3-ene-1-carbaldehyde gave previously unknown 1,7-phenanthroline derivatives. The reactions in butan-1ol were characterized by 100% regioselectivity but low stereoselectivity, and mixtures of cis-and trans-isomeric methyl 7-aryl(hetaryl, cyclohexenyl)-10, 10-dimethyl-8-oxo-7,8,9,10,11,12-hexahydrobenzo[b][1,7]phenanthroline-9-carboxylates were obtained at a ratio of ~45 : 55.Reactions of amines of the quinoline series with carbonyl-containing compounds are widely used in the synthesis of phenanthrolines. We previously showed [1-4] that quinolin-6-amine reacts with aromatic aldehydes and methyl or methylene ketones (CH acids) to give various 4,7-phenanthroline derivatives. It was also found that cyclic 1,3-diketones are the most efficient reagents among CH acids [3,4]. Partly hydrogenated oxo derivatives of benzo[b][4,7]phenanthroline obtained as a result of the above reactions attract interest as analogs of natural alkaloids, enzyme inhibitors, bactericidal agents, and antibiotics [5][6][7][8].In the present work we were the first to perform three-component condensation of quinolin-5-amine (I) with methyl 2,2-dimethyl-4,6-dioxocyclohexane-1-carboxylate (II) and substituted benzaldehydes, thiophene-2-carbaldehydes, and cyclohex-3-ene-1-carbalehyde IIIa-IIIs with a view to obtain previously unknown fused 1,7-phenanthroline derivatives (structural analogs of previously synthesized benzo[b][4,7]phenanthrolines) as potential biologically active substances [9, 10]. The condensation was performed by heating equimolar amounts of the reactants in boiling butan-1-ol. Due to high reactivity of β-dicarbonyl compound II, its condensation with amine I and aldehydes III in alcoholic medium required no catalyst. Presumably, the reaction was catalyzed by proton formed via ionization of the enol tautomer of β-diketone II. As a result, the corresponding stereoisomeric 7-substituted methyl 10, 10-dimethyl-8-oxo-7,8,9,10,11,12-hexahydrobenzo[b][1,7]phenanthroline-9-carboxylates IVa-IVs and Va-Vs were formed in 37-80% yield with high regioselectivity.By analogy with our previous data [11] on the three-component condensation of naphthalen-1-amine (a carbocyclic analog of quinolin-5-amine) with aromatic aldehydes and 5,5-dimethylcyclohexane-1,3-dione (dimedone), we presumed that the fused benzo[b]-[1,7]phenanthroline system is formed via initial reaction of amine I with aldehyde III. The subsequent addition of diketone II at the C=N bond of Schiff base A yields intermediate B which undergoes HofmannMartius type rearrangement (migration of the N-alkyl substituent in aniline into aromatic ring [12]), followed by cyclocondensation of rearrangement product E.Transformation of intermediate B may also involve its hydramine fission into initial amine I and α,β-unsaturated ketone D. The exocyclic double bond in the latter is strongly activated due to conjugation with two neighboring carb...

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

Cited by 14 publications

References 4 publications

Pyridoacridines in the 21st Century

Pyridoacridines in the 21st Century

Synthesis and Mechanistic Study of Triheterocyclic 4H‐Pyrimido[2,1‐b]benzothiazole derivatives, One‐Pot Three‐component Reaction under Solvent‐Free Conditions

Synthesis of methyl 7-aryl(hetaryl, cyclohexenyl)-10,10-dimethyl-8-oxo-7,8,9,10,11,12-hexahydrobenzo[b][1,7]phenanthroline-9-carboxylates

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