A convenient access to furo[3,2-c]pyridin-6(5H)-ones by the reaction of 5-iodo-4-methoxy-2-pyridones with terminal alkynes under microwave-enhanced Sonogashira conditions

Conreaux, David; Delaunay, Thierry; Desbordes, Philippe; Monteiro, Nuno; Balme, Geneviève

doi:10.1016/j.tetlet.2009.02.073

Cited by 15 publications

(8 citation statements)

References 7 publications

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“…Stereochemical disposition of trans H's were confirmed by 2D NMR vis HSQC and HMBC. As anticipated all the 19 signals are appeared in 13 C NMR spectrum. HRMS spectra shows molecular ion (M+ Na) peak at 412.1515.…”

Section: Resultssupporting

confidence: 80%

“…The structure of the compound was characterized by 1 H and 13 C NMR, MS and IR spectra and elemental analysis. In the 1 H NMR spectra, the two protons at 2,3-position of dihydrofuran ring display two doublets at 5.41 and 4.44 ppm with the vicinal coupling constant J = 4.6 and 4.6 Hz, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…Column chromatography was performed on silica gel (100-200 mesh, SRL Chemicals) using increasing percentage of ethyl acetate in hexanes. 1 H NMR spectra (400 MHz) and 13 C NMR (100 MHz) and DEPT-135 spectra were recorded for CDCl3 + CCl4 (2:1) solutions on a Bruker-400 spectrometer with tetramethylsilane (TMS) as internal standard; J values are given in Hz. IR spectra were recorded as KBr solid solution on a Nicolet-6700 spectrometer.…”

Section: Melting Pointsmentioning

confidence: 99%

“…Most of them may suffer from tedious steps, low yields and poor region and stereoselectivity [9][10][11][12][13][14][15][16][17]. Recently we have developed two new methodologies for the synthesis of C3-dihydrofuran substituted coumarins, dihydrofuro pyrazole by employing one pot multicomponent synthesis with pyridinium ylide.…”

Section: Introductionmentioning

confidence: 99%

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One Pot Multicomponent Synthesis of Anti-inflammatory Active Tetrahydrofuro[3,2-c]pyridinone-2-carboxylate Derivatives

Tangeti¹,

Reddy²,

Evangeline³

2018

Asian J. Chem.

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A novel, one-pot method has been developed for the synthesis of tetrahydrofuro[3,2-c]pyridine-2-carboxylate derivatives via cascade four-component condensation of 6-methyl, 4-hydroxy pyranone, aryl amines, aromatic aldehydes and pyridinium ylide, in presence of triethylamine as a catalyst under ethanol reflux conditions. It affords the corresponding product in high yield (78-92 %) with short reaction time (15-25 min).The anti-inflammatory activity of these compounds was determined. Out of the 17 synthesized compounds, compounds 5j, 5k, 5l, 5m and 5n were excellent inhibitors of TNF-α and IL-6, COX-2, β-glucuronidase.

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Section: Resultssupporting

confidence: 80%

Section: Resultsmentioning

confidence: 99%

Section: Melting Pointsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

One Pot Multicomponent Synthesis of Anti-inflammatory Active Tetrahydrofuro[3,2-c]pyridinone-2-carboxylate Derivatives

Tangeti¹,

Reddy²,

Evangeline³

2018

Asian J. Chem.

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“…The Heck cross‐coupling of 3‐iodoquinolin‐4(1 H )‐one with styrene was found to work well with N ‐methyl derivative than the corresponding NH‐4‐oxo precursor . Palladium‐catalyzed cross‐coupling of halogenated quinolinones with terminal alkynes or alkenes and subsequent heteroannulation of the incipient tethered derivatives, on the other hand, has become an important tool for the construction of polynuclear derivatives . Pal et al .…”

Section: Introductionmentioning

confidence: 99%

2,6,8‐Triaryl‐3‐iodoquinolin‐4(1H)‐ones as Substrates for the Synthesis of 2,3,6,8‐Tetraarylquinolin‐4(1H)‐ones and the 2‐Substituted 4,6,8‐Triaryl‐1H‐furo[3,2‐c]quinolines

Mphahlele

2016

Journal of Heterocyclic Chem

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Copper‐ and Ligand‐free Heteroannulation of o‐Halohydroxypyridine with Terminal Alkynes Using Pd/C Catalyst: One‐Pot Synthesis of 2‐Substituted Furopyridines and their Functionalization

Park

Kim

Yum

et al. 2015

Bulletin Korean Chem Soc

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Three types of isomeric 2-substituted furo [3,2-b]pyridine, furo [2,3-b]pyridine and furo[3,2-c]pyridine were prepared using Pd/C-catalyzed heteroannulation of o-halopyridinols and terminal alkynes under copperand ligand-free conditions. We also demonstrated that double functionalization yielding 2,3-disubstituted furopyridines could be achieved through heteroannulation followed by bromination and Suzuki/Heck reactions. In addition, the use of recoverable Pd/C in the absence of a cocatalyst and ligand can aid in the development of greener chemical processes.

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A convenient access to furo[3,2-c]pyridin-6(5H)-ones by the reaction of 5-iodo-4-methoxy-2-pyridones with terminal alkynes under microwave-enhanced Sonogashira conditions

Cited by 15 publications

References 7 publications

One Pot Multicomponent Synthesis of Anti-inflammatory Active Tetrahydrofuro[3,2-c]pyridinone-2-carboxylate Derivatives

One Pot Multicomponent Synthesis of Anti-inflammatory Active Tetrahydrofuro[3,2-c]pyridinone-2-carboxylate Derivatives

2,6,8‐Triaryl‐3‐iodoquinolin‐4(1H)‐ones as Substrates for the Synthesis of 2,3,6,8‐Tetraarylquinolin‐4(1H)‐ones and the 2‐Substituted 4,6,8‐Triaryl‐1H‐furo[3,2‐c]quinolines

Copper‐ and Ligand‐free Heteroannulation of o‐Halohydroxypyridine with Terminal Alkynes Using Pd/C Catalyst: One‐Pot Synthesis of 2‐Substituted Furopyridines and their Functionalization

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