A general synthesis of quinolinones and benzothiazine 1,1-dioxides via ring closing metathesis

Minville, Joannie; Poulin, Jason; Dufresne, Claude; Sturino, Claudio F.

doi:10.1016/j.tetlet.2008.03.144

Cited by 50 publications

(31 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Quinolines and their analogues are considered as an important class of bioactive heterocyclic compounds because of its versatile applications in the field of pharmaceuticals and in various biological systems [1][2][3][4][5]. Quinoline scaffolds because of their varied biological activities like antimicrobial, antioxidant, antimalarial (chloroquine and mefloquine), anticancer, antiinflammatory, cytotoxic agents, tyrosine kinase PDGF-RTK inhibitor and topoisomerase I inhibitors have great significance among heterocycles [4][5][6][7][8]. In addition to medicinal applications, quinoline derivatives are found to undergo hierarchical self-assembly into a variety of nano-structures and meso-structures with enhanced electronic and photonic functions [9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Molecular Modelling and in Vitro Hypoglycemic Examination of Polysubstituted Quinoline Derivatives

Angajala¹,

Aruna²,

Subashini³

et al. 2019

IJEAT

View full text Add to dashboard Cite

In the present work in-silico molecular simulations were carried out to find out the binding affinities of synthesized polysubstituted quinolines towards PPARγ protein (2XKW). The results obtained from docking analysis showed that the synthesized polysubstituted quinoline derivatives 1a-g are having stronger binding interactions which was on par to that of standards rosiglitazone and pioglitazone. In addition to this in-vitro hypoglycemic studies were studied through α-amylase and α-glucosidase enzyme inhibition assays. The results showed that compounds 1c and 1d possess good hypoglycemic efficacy with percentage inhibition of 87.94 ± 0.25, 85.90 ± 0.56 towards α-glucosidase and 84.55 ± 1.02, 82.14 ± 0.26 percent inhibition towards α-amylase which was greater than standard rosiglitazone and comparable to standard pioglitazone

show abstract

Section: Introductionmentioning

confidence: 99%

Molecular Modelling and in Vitro Hypoglycemic Examination of Polysubstituted Quinoline Derivatives

Angajala¹,

Aruna²,

Subashini³

et al. 2019

IJEAT

View full text Add to dashboard Cite

show abstract

“…On the other hand, only few examples of metal-catalyzed strategies which provide more powerful and practical route to heterocycles, are reported for construction of substituted quinolones. [48][49][50][51][52][53][54][55][56][57][58][59][60] Some recent developments in metal-catalyzed construction of these privileged scaffolds include cycloaddition of o-cyanophenylbenzamides [61][62] and Narylcarbamoyl chlorides 63 with internal alkynes, ring closing metathesis (RCM) reaction of Nphenylacrylamides, 64 domino Heck/Buchwald-Hartwig reaction of o-bromocinnamamide and iodoarenes 65 and cyclization of 3,3-diarylacrylamides through intramolecular C-H amination 66 which often require employing complicated starting materials. Larock et al developed a palladium-catalyzed carbonylative annulation of alkynes with readily available anilines employing gaseous CO.…”

Section: Introductionmentioning

confidence: 99%

Carbonylative annulation of unsaturated compounds using molybdenum hexacarbonyl: an efficient synthesis of 2(1H)-quinolones

Jafarpour¹,

Otaredi-Kashani²

2014

Arkivoc

View full text Add to dashboard Cite

A ligand-and CO gas-free condition is developed in palladium-catalyzed three-component reaction of iodoanilines, unsaturated compounds and Mo(CO) 6 as a solid carbon monoxide source. The approach allows for smooth construction of biologically interesting 3,4-disubstituted (dihydro)quinolin-2(1H)-ones in presence of catalytic amounts of palladium and avoids the problematic use of gaseous carbon monoxide.

show abstract

“…The mixture was stirred at 80°C for 16 h. After TLC indicated completion of the reaction, the reaction mixture was cooled to room temperature, quenched with NaHCO 3 , and extracted with EtOAc (2 ϫ 10 mL). 1 [22] [23] 253 mg, 80 % yield. The residue was purified by column chromatography (silica gel, 2-4 % MeOH in CH 2 Cl 2 ) to give 5a (95.4 mg, 60 %).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Substituted Coumarins and 2‐Quinolinones by Cycloisomerisation of (Hydroxy/aminophenyl)propargyl Alcohols

2012

View full text Add to dashboard Cite

A new cycloisomerization strategy for the synthesis of coumarins and quinolinones is described. The addition of ethoxyacetylide to 2‐hydroxyacetophenones directly resulted in 4‐substituted coumarins by 6‐endo‐dig cycloisomerisation of the intermediate 3‐ethoxy‐1‐(2‐hydroxyphenyl)‐2‐propyn‐1‐ols. Under similar conditions, 2‐aminoacetophenone produced 2‐ethoxyquinoline, a masked quinolinone, which was converted into the quinolinone by acid treatment. N‐Protected intermediate 8 was isolated and converted into the quinolinone [with In(OTf)3 or H2SO4] or the 3‐iodo‐2‐quinolinone (with I2 and H+).

show abstract

A general synthesis of quinolinones and benzothiazine 1,1-dioxides via ring closing metathesis

Cited by 50 publications

References 46 publications

Molecular Modelling and in Vitro Hypoglycemic Examination of Polysubstituted Quinoline Derivatives

Molecular Modelling and in Vitro Hypoglycemic Examination of Polysubstituted Quinoline Derivatives

Carbonylative annulation of unsaturated compounds using molybdenum hexacarbonyl: an efficient synthesis of 2(1H)-quinolones

Synthesis of Substituted Coumarins and 2‐Quinolinones by Cycloisomerisation of (Hydroxy/aminophenyl)propargyl Alcohols

Contact Info

Product

Resources

About