Highly Diastereoselective Inverse Electron Demand (IED) Diels—Alder Reaction Mediated by Chiral Salen—AlCl Complex: The First, Target‐Oriented Synthesis of Pyranoquinolines as Potential Antibacterial Agents.

Magesh, Chinnian J; Makesh, Sarasu V; Perumal, Paramasivan T.

doi:10.1002/chin.200435130

Cited by 2 publications

(2 citation statements)

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“…[14] Some of the naturally occurring alkaloids (flindersine, oricine, and verprisine) contain both the above heterocycles in the form of pyranoquinoline moiety and possess various biological activities. [15][16][17] According to literature, there were a variety of three or four component reactions for the construction of different pyrano quinoline carbonitriles. [18] Among them a three component reaction between aromatic aldehyde, malononitrile, and 8-hydroxy quinoline in ethanol was reported with a variety of catalysts.…”

Section: Original Articlementioning

confidence: 99%

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Siliveri¹

2017

IJGP

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Aim: To synthesize novel pyrano quinolines by one-pot multicomponent reaction under noncatalytic conditions, further it was proposed to investigate the reactivity of pyrano quinolines with the oxidizing agent like iodobenzene diacetate (IBD). Synthesized compounds were evaluated for antibacterial activity. Materials and Methods: Synthetic procedure: A mixture of aldehyde (1 mmol), malononitrile (1 mmol) in 10 ml of ethanol-water (1:1) was stirred for 10 min and then followed by addition of 8-hydroxy quinoline (1 mmol) and refluxed at 100°C for 1-2 h. The precipitated solid was collected by filtration. In the next step, to a suspension of pyrano[3,2-h]quinoline carbonitrile (1 mmol) in 5 mL of alcohol was added IBD (1.1 mmol) with stirring at room temperature open to air. The reaction mixture immediately became a clear solution followed by the precipitation of the product. The mixture was filtered and washed with the corresponding alcohol to afford the desired product. Antibacterial activity: All the synthesized compounds were screened for antimicrobial activity at a concentration of 100 µg/50 µl using ciprofloxacin as a standard drug. The minimum inhibitory concentrations (MICs) of these compounds were determined using broth microdilution MIC method. Results and Discussion: Synthetic studies: At the outset, pyrano[3,2-h]quinoline carbonitrile analogs 1(a-j) were constructed by a catalyst-free protocol via a one-pot, three-component condensation. Further, catalytic oxidative difunctionalization of the chromene double bond was achieved using hypervalent iodine reagents such as IBD in alcoholic medium and total 14 novel compounds 2(a-k) have been synthesized and confirmed on the basis of spectral data (infrared, nuclear magnetic resonance, and mass). Antibacterial activity: Among all the tested compounds, 1g, 1h, 1j, 2d, 2f, 2h, and 2k showed antibacterial activity against both Gram-positive and Gram-negative standard strains, and their MICs ranged between 1.56 and 12.55 µg/mL. Conclusion: In summary, an efficient, economical and eco-friendly multicomponent protocol for the construction of pyrano[3,2-h]quinoline carbonitriles has been achieved, and an oxidative difunctionalization of chromene double bond has been studied in the alcoholic solvent medium in the presence of IBD.

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Section: Original Articlementioning

confidence: 99%

Untitled

Siliveri¹

2017

IJGP

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“…The preparation of pyranoquinolines has received significant attention (Kamal et al,2004;Yadav et al, 2002;Nagarajan et al, 2001) in previous years because of the broad spectrum of their biological properties such as psychotropic, antiallergic, antiinflammatory and estrogenic activities (Yamada et al, 1992;Faber et al, 1984). In addition, pyranoquinoline derivatives are found to possess a wide range of pharmacological activity (Magesh et al,2004). Further, several bioactive alkaloids which are widely distributed in nature contain a pyranoquinoline moiety (Ih-Sheng Chen et a.,l 1997;Dagne et al, 1988).…”

Section: Introductionmentioning

confidence: 99%

The effective reaction of 2-chloro-3-formylquinoline and acetic acid/sodium acetate under microwave irradiation

Nadaraj¹,

Selvi²

2011

Int. J. Eng. Sci. Tech

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Pyrano[2,3-b]quinolin-2-ones have been synthesized efficiently from 2-chloro-3-formylquinolines in a single step by treating with sodium acetate and acetic acid under microwave irradiation. The structures of the compounds have been established by IR, NMR and mass spectral data. Unexpectedly, 3-formylquinolin-2(1H)-ones were exclusively formed in very high yields by changing the molar ratio of acetic acid and sodium acetate in just 1.5 to 2.5 min.

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Highly Diastereoselective Inverse Electron Demand (IED) Diels—Alder Reaction Mediated by Chiral Salen—AlCl Complex: The First, Target‐Oriented Synthesis of Pyranoquinolines as Potential Antibacterial Agents.

Cited by 2 publications

References 1 publication

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The effective reaction of 2-chloro-3-formylquinoline and acetic acid/sodium acetate under microwave irradiation

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