Synthesis of novel bis-condensed heterocyclic ring assembly systems

Sachar, Anand; Sharma, Rohit; Kumar, Surinder; Kaur, Daljeet; Singh, J. B.

doi:10.1002/jhet.5570430507

Cited by 8 publications

(2 citation statements)

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“…The products were isolated and characterized by physical and spectral data and they were compared with authentic samples (Table 1). 9,10,[15][16][17][18][19][20][21][22][23][24][25][26] General procedure for preparation of Fe 3 O 4 nanoparticles To prepare Fe 3 O 4 nanoparticles, 5.2 g of FeCl 3 and 2.0 g of FeCl 2 were successively dissolved in 25 mL of distilled water containing 0.85 mL of 12.1 N HCl. The resulting solution was added dropwise into 250 mL of 1.5 M NaOH solution under vigorous stirring.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of xanthene derivatives by employing Fe3O4nanoparticles as an effective and magnetically recoverable catalyst in water

Karami

Hoseini

Eskandari

et al. 2012

Catal. Sci. Technol.

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Section: Methodsmentioning

confidence: 99%

Synthesis of xanthene derivatives by employing Fe3O4nanoparticles as an effective and magnetically recoverable catalyst in water

Karami

Hoseini

Eskandari

et al. 2012

Catal. Sci. Technol.

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“…Literature survey reveals that a fair amount of work has been published in the condensation reactions of barbituric acid, dimedone, and other active methylene carbocyclic and heterocyclic compounds. Because of long standing interest in our laboratory in the condensation reactions of active methylene compounds [21][22][23] and generation of new fused (''ortho'' and ''ortho and peri''), bridged [23], spiro [24], ring assembly and cyclophane [25] heterocyclic compounds, we have extended our synthetic activity along these lines to include the synthesis of some pyridopyrimidine, pyrimidonaphthyridine, benzo [b]pyrimidonaphthyridine, dipyrimidonaphthyridine, pyrimidonaphthyridinoquinazoline, pyrimidonaphthyridinobenzodiazepine, pyridopyrimido-pyrimido-naphthyridine, pyrimidonaphthyridino-pyridoquinazoline, and 1,3,4,6,7,8,9,11-octazabenzo[de]naphthacene systems.…”

Section: Introductionmentioning

confidence: 99%

Facile and one pot synthetic routes for various novel, differently fused and promising heteropolycycles

Gupta

Sachar

et al. 2010

Journal of Heterocyclic Chem

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Synthesis of Novel Bis‐Condensed Heterocyclic Ring Assembly Systems.

et al. 2007

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The novel bis-condensed heterocyclic systems with ring assemblies based on peripheral barbituric acid rings and central pyran, pyridine and thiine rings have been generated by the reaction of terephthalaldehyde and isophthalaldehyde with barbituric acid for comparison with the analogous systems generated with said dialdehydes and 1,3-cyclohexanedione. Carbonyl compounds especially the aldehydes and to large extent ketones also condense with cyclic reactive methylene compounds to produce olefins [1][2]. This is an excellent method for generation of carbon-carbon double bonds. These reactions are generally base or acid catalysed. Literature search reveals that a fair amount of work has been published on the reaction of aromatic monoaldehyde with active methylene compounds [3][4][5][6][7][8][9]. In the present article, we are reporting and highlighting the reaction of barbituric acid as an active methylene pyrimidine derivative with terephthalaldehyde and isophthalaldehyde in N,N-dimethyl formamide (DMF). When terephthalaldehyde and isophthalaldehyde were treated with barbituric acid under different conditions novel pyran, pyridine and thiine based heterocyclic ring assemblies were generated probably via the intermediacy of normal Knoevenagel reaction, Michael addition and cyclodehydratioon. With phthalaldehyde, a mixture of products was obtained and due to poor yield because of over crowding, the products could not be separated.When the two aromatic dialdehydes were treated with 1,3-cyclohexanedione under different conditions in ethylene glycol as reported [10] with dimedone and [11] for the synthesis of bifunctional pyridine and quinoline derivatives under similar conditions; bis-xanthene, bisacridine and bis-thioxanthene ring assemblies were generated as expected. Comparative yields in two different solvent systems for two sets of reactions have been recorded in Table 1. The reactions are shown in Scheme 1. All the compounds obtained gave analysis for C, H, N and S in good agreement with calculated values, and the structures were established on the basis of spectroscopic data.Results and Discussion.Using only terephthalaldehyde and barbituric acid in DMF as such; in presence of NH 4 OAc, NH 2 OH.HCl, and NaOAc and P 2 S 5 , the condensed ring assembly compounds 2a, 3a, 4a and 5a respectively were obtained in good yield under thermal conditions. Using isophthalaldehyde and barbituric acid under exactly similar conditions the novel compounds 2b, 3b, 4b and 5b were obtained. With 1,3-cyclohexanedione and terephthalaldehyde under analogues conditions using ethylene glycol solvent, the ring assembly compounds 6a,7a, 8a and 9a were obtained. 1,3-Cyclohexanedione and isophthalaldehyde under different conditions in the ethylene glycol furnished the compounds 6b, 7b ,8b and 9b.It has been summarised under the present exposition that DMF is suitable solvent for barbituric acid as a synthon and ethylene glycol is the most suitable solvent for cyclohexanedione as the synthon. P 2 S 5 in the synthesis of thio compunds 5a, 5b,...

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Synthesis of novel bis-condensed heterocyclic ring assembly systems

Cited by 8 publications

References 10 publications

Synthesis of xanthene derivatives by employing Fe3O4nanoparticles as an effective and magnetically recoverable catalyst in water

Synthesis of xanthene derivatives by employing Fe3O4nanoparticles as an effective and magnetically recoverable catalyst in water

Facile and one pot synthetic routes for various novel, differently fused and promising heteropolycycles

Synthesis of Novel Bis‐Condensed Heterocyclic Ring Assembly Systems.

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