86-83-9

Usage

InChI:InChI=1/C14H13NO2/c1-10(16)9-14(17)15-13-8-4-6-11-5-2-3-7-12(11)13/h2-8H,9H2,1H3,(H,15,17)

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 134-32-7 1-amino-naphthalene 
• 141-97-9 ethyl acetoacetate 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 1210-07-7 4-methyl-benzo[h]quinolin-2-ol 
• 455927-35-2 C₂₂H₁₈ClN₃OS 
• 455927-88-5 C₂₃H₂₁N₃O₂S 
• 1172995-92-4 C₂₂H₁₉N₃O₂S 
• 1172995-88-8 C₂₄H₂₄N₄OS 
• 1159801-52-1 5-cyano-2-methyl-4-(4-methylphenyl)-N-1-naphthyl-(6-thioxo-1,6-dihydropyridine)-3-carboxamide 
• 1159801-48-5 4-(4-chlorophenyl)-5-cyano-2-methyl-N-1-naphthyl-6-thioxo-1,6-dihydropyridine-3-carboxamide 
• 1159801-55-4 5-cyano-4-(4-methoxyphenyl)-2-methyl-N-1-naphthyl-6-thioxo-1,6-dihydropyridine-3-carboxamide 
• 1210-07-7 4-methyl-2(1H)-benzoquinolinone 
• 1093168-21-8 C₁₈H₁₉NO₂ 

Relevant academic research and scientific papers

Synthesis and in vitro Antidiabetic Screening of Novel Dihydropyrimidine Derivatives

Abstract: A series of N-substituted-6-methyl-4-{4-[5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]methoxyphenyl}-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides have been synthesized by the condensation of newly synthesized {4-[5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]methoxy}benzaldehyde with variously substituted acetoacetanilides and urea in the presence of ethanol. The synthesized compounds have been characterized by 1H, 13C NMR, IR spectroscopy, and mass spectrometry. All synthesized compounds were evaluated for in vitro antidiabetic activity using the α-amylase inhibition assay with the 3,5-dinitrosalicylic acid (DNSA) reagent.

Synthesis of β-Ketoamide Curcumin Analogs for Anti-Diabetic and AGEs Inhibitory Activities

Two different series of novel β-ketoamide curcumin analogs enriched in biological activities have been synthesized. The synthesized compounds were screened for their in?vitro anti-diabetic and AGEs inhibitory activities and exhibited potent to good anti-diabetic and AGEs inhibitory activities. The molecular docking study was also performed with the α-amylase enzyme.

Preparation of Pincer 4-Functionalized 2-Aminomethylbenzo[h]quinoline Ruthenium Catalysts for Ketone Reduction

Reaction of 1-naphthylamine with ethyl benzoylacetate gives the corresponding benzoyl acetamide derivative 1, which undergoes cyclization to 4-phenylbenzo[h]quinolin-2(1H)-one (2) in the presence of H2SO4. Bromination with POBr3, followed by reaction with n-BuLi and DMF, gives 4-phenylbenzo[h]quinoline-2-carbaldehyde (4), which is converted to the corresponding oxime hydrochloride 5 with NH2OH·HCl. Hydrogenation of 5 catalyzed by 10% Pd/C (type 338) leads to 4-phenyl-2-aminomethylbenzo[h]quinoline hydrochloride (HCNNPh·HCl, 6) isolated in high yield. Similarly, the 4-methyl-2-aminomethylbenzo[h]quinoline derivative (HCNNMe·HCl, 12) is prepared starting from 1-naphthylamine and 2,2,6-trimethyl-4H-1,3-dioxin-4-one, following the route for 6. Reaction of RuCl2(PPh3)3 with a diphosphine (PP), the HCl salt 6, and NEt3 in 2-propanol leads to the pincer complexes RuCl(CNNPh)(PP) (PP = Ph2P(CH2)3PPh2, 13; Ph2P(CH2)4PPh2, 14; 1,1′-bis(diphenylphosphino)ferrocene, 15). The methyl derivatives RuCl(CNNMe)(PP) (PP = Ph2P(CH2)3PPh2, 16; Ph2P(CH2)4PPh2, 17; 1,1′-bis(diphenylphosphino)ferrocene, 18) are obtained in a similar way using 12 in place of 6. Treatment of [RuCl2(p-cymene)]2 with rac-BINAP, 6, and NEt3 affords RuCl(CNNPh)(BINAP) (19), isolated as a mixture of two diastereoisomers (3:4 molar ratio). The chiral RuCl(CNNPh)[(S,R)-JOSIPHOS] (20) is obtained as a single isomer from [RuCl2(p-cymene)]2, (S,R)-JOSIPHOS, and 6. Complexes 13-20 efficiently catalyze the transfer hydrogenation of acetophenone in 2-propanol at reflux in the presence of NaOiPr (2 mol%) with S/C = 5000-20-000 and at high rate (TOF up to 6.7 × 103 min-1). With complexes 13, 15, 17, and 18 several ketones of commercial-grade purity have been reduced to alcohols, including the bulky RCO(tBu) (R = Me, Ph) substrates. With 20 acetophenone is reduced to (S)-1-phenylethanol with 85% ee. The pincer complexes 13-15 and 18 are also found highly active in the hydrogenation of ketones at 40 °C with an S/C = 10-000, under 5 bar of dihydrogen in methanol and in the presence of 2 mol % of a base (NaOH, KOH, NaOMe).

BENZO[H]QUINOLINE LIGANDS AND COMPLEXES THEREOF

The present invention provides substituted tridentate benzo[h]quinoline ligands and complexes thereof. The invention also provides the preparation of the ligands and the respective complexes, as well as to processes for using the complexes in catalytic reactions.