2415-85-2Relevant articles and documents
Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones
Daniliuc, Constantin,Glorius, Frank,Hu, Tianjiao,Lückemeier, Lukas
supporting information, p. 23193 - 23196 (2021/09/25)
Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three-dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)-NHC-catalyzed asymmetric hydrogenation of 2-quinolones under mild reaction conditions. Alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones.
Synthesis and anticonvulsant activity of some 1,4-dihydropyridine derivatives
Begum, Safia,Sirisha, Kalam
, p. 433 - 438 (2021/09/28)
A series of asymmetrical 4-alkyl/aryl-2,6-dimethyl-3-N-(aryl/heteroaryl)-carbamoyl-5-ethoxycarbonyl-1, 4-dihydropyridines 3a-d and symmetrical 4-alkyl/aryl-2,6-dimethyl-3,5-bis-(ethoxycarbonyl)-1,4-dihydropyridines 4a and 4b have been prepared by the condensation of various benzaldehydes, ethylacetoacetate, 2-aminopyridine or p-toludine in ethanol (Hantzch method). The structures of all the synthesized 1,4-dihydropyridine derivatives have been confirmed by spectral data (IR,1H NMR) and elemental analysis. Compounds 3a-c, 4a and 4b (10 mg/kg) have been evaluated for their anticonvulsant effect against pentylenetetrazole- induced convulsions with phenytoin (4 mg/kg) as the standard. The anticonvulsant potential of the newly synthesized compounds have been assessed on the basis of increase in latency (onset time) to induce convulsions; decrease in number of convulsions and increase in latency of death compared to control and standard.
HFIP-mediated strategy towards β-oxo amides and subsequent Friedel-Craft type cyclization to 2?quinolinones using recyclable catalyst
Kabi, Arup K.,Gujjarappa, Raghuram,Vodnala, Nagaraju,Kaldhi, Dhananjaya,Tyagi, Ujjawal,Mukherjee, Kalisadhan,Malakar, Chandi C.
supporting information, (2020/10/20)
A simple and cost-effective 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)-mediated protocol for the synthesis of β-oxo amides has been described by using amines and β-keto esters as substrates. The reaction conditions were found to be highly efficient towards the cleavage of C[sbnd]O bond and consequent formation of the products in excellent yields and selectivity. The obtained β-oxo amides were further transformed in to the synthetically useful 2?quinolinones via intramolecular Friedel-Craft type cyclization of aromatic ring using ferrites as a recyclable catalyst. A spectrum of substrates bearing broad range of functional groups were well tolerated under the reaction conditions. The proposed mechanistic pathways were substantially verified by literature and mass-spectroscopic evidences.
