Tetrahydropyran‐2,4‐diones in the Synthesis of Fused N,O‐Heterocycles.

Козлов, Н. Г.; Pashkovskii, F. S.; Tereshko, A. B.; Lokot, I. P.; Gusak, K. N.; Лахвич, Ф. А.

doi:10.1002/chin.200327131

Cited by 3 publications

(3 citation statements)

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“…The hetero analogs of β-diketones -tetrahydrofuran-2,4-dione (tetronic acid), 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid), 6-methyl-, 6,6-dimethyl-, 6-phenyl-, 6-spirocyclooctyltetrahydropyran-2,4-dioneswere first used as synthons for triple-component condensation in [98][99][100][101][102][103].…”

Section: Synthesis Of Condensed Heterocycles With Two Different Hetermentioning

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: Synthesis Of Condensed Heterocycles With Two Different Hetermentioning

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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“…This reaction was successfully used to prepare various functionalized derivatives of piperidine [1], benzo[f]quinoline [2], benzoacridine [3,4], phenanthroline [5], pyrazolo [3,4-b]quinoline [6], pyrimido [4,5-b]quinoline [7], furo [3,4-e]pyrazolo [3,4-b]pyridine [8], and other heterocyclic systems [9]. In all cases, the starting compounds were electron-rich aromatic monoamines.…”

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confidence: 99%

Heterocyclization of N,N′-disubstituted p-phenylenediamines with cyclich β-diketones and formaldehyde. Synthesis of new pyrido[2,3-g]quinoline derivatives

2011

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Three-component condensation of N,N′-dibenzyl-p-phenylenediamines with cyclic β-diketones and formaldehyde under mild conditions resulted in selective formation of a series of new dispiro derivatives of pyrido[2,3-g]quinoline.Three-component condensation of aromatic amines with aldehydes and cyclic β-dicarbonyl compounds provides a convenient one-step procedure for the synthesis of fused polynuclear heterocyclic systems. This reaction was successfully used to prepare various functionalized derivatives of piperidine [1], benzo[f]quinoline [2], benzoacridine [3, 4], phenanthroline [5], pyrazolo[3,4-b]quinoline [6], pyrimido[4,5-b]quinoline [7], furo[3,4-e]pyrazolo[3,4-b]pyridine [8], and other heterocyclic systems [9]. In all cases, the starting compounds were electron-rich aromatic monoamines.We previously showed that spiro compounds of the 1,2,3,4-tetrahydroquinoline series can readily be obtained by condensation of N-monosubstituted anilines I containing an electron-donating substituent R 1 with formaldehyde (II) and cyclic β-diketones III (Scheme 1) [10]. We presumed that analogous three-component condensation may be performed with aromatic diamines. In this case, the second amino group should not only activate the reaction due to its pronounced electron-donor properties but also participate in condensation, giving rise to new polynuclear nitrogencontaining heterocycles. To verify this assumption, we synthesized a series of symmetric N,N′-disubstituted p-phenylenediamines Ia-If and brought them into three-component condensation with formaldehyde (II) and cyclic β-diketones IIIa and IIIb of the cyclohexane-1,3-dione series. The reactions were carried out in ethanol by heating for a short time in the absence of a catalyst. In fact, the products were those formed from one aromatic diamine molecule and two β-diketone and two formaldehyde molecules. On the basis of the 1 H NMR data, the isolated compounds were assigned the structure of pyrido[2,3-g]quinoline derivatives VIa-VIl (Scheme 2). It should be noted that alternative isomeric heterocyclization products, 4,7-phenanthroline derivatives like VII, were not detected in the reaction mixtures.A probable mechanism of the heterocyclization process is shown in Scheme 3. Spirocyclic pyrido-[2,3-g]quinoline derivatives VIa-VIl are formed via initial reaction of formaldehyde (II) with β-diketone

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“…Compounds Va and Vb were also synthesized by three-component condensation of aldehyde Ia with naphthalen-2-amine and the corresponding diketone. In the recent time, three-component condensations have become more and more important as efficient and selective synthetic routes to fused nitrogencontaining heterocycles [10][11][12][13].…”

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Synthesis and properties of (E)-4-[alkyl(aryl)iminomethyl]-2-methoxy(ethoxy)phenyl adamantane-1-carboxylates

2010

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Condensation of 4-formyl-2-methoxy(ethoxy)phenyl adamantane-1-carboxylates with aliphatic, cycloaliphatic, and aromatic amines gave the corresponding adamantane-containing Schiff bases as E isomers with respect to the CH=N azomethine bond. The reaction of 2-methoxy-4-(naphthalen-2-yliminomethyl)phenyl adamantane-1-carboxylate with cyclohexane-1,3-dione and dimedone led to the formation of 2-methoxy-4- (11-oxo-7,8,9,10,11,12-hexahydrobenzo[a]acridin-12-yl)phenyl adamantane-1-carboxylates. Quantum-chemical calculations of the energies of formation of E and Z isomers of some of the synthesized Schiff bases were performed.

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Tetrahydropyran‐2,4‐diones in the Synthesis of Fused N,O‐Heterocycles.

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 3 publications

References 1 publication

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)*

Heterocyclization of N,N′-disubstituted p-phenylenediamines with cyclich β-diketones and formaldehyde. Synthesis of new pyrido[2,3-g]quinoline derivatives

Synthesis and properties of (E)-4-[alkyl(aryl)iminomethyl]-2-methoxy(ethoxy)phenyl adamantane-1-carboxylates

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