1210-07-7

Upstream product

• 134-32-7 1-amino-naphthalene 
• 86-83-9 N-1-naphthyl-3-oxobutyramide 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 61773-06-6 2-chlor-4-methylbenzo-quinoline 
• 40174-37-6 4-methyl-7,8-benzoquinoline 
• 6707-23-9 benzo[h]quinoline-4-carboxylic acid 
• 31493-12-6 4-styryl-benzo[h]quinoline 
• 7498-19-3 4-(trans-2-benzo[h]quinolin-4-yl-vinyl)-N,N-dimethyl-aniline 

Relevant academic research and scientific papers

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.

Substituent effects on absorption and fluorescence spectra of carbostyrils

Absorption and fluorescence spectra as well as quantum yields of a series of differently substituted carbostyrils (quinolin-2(1H)-ones) are reported. Especially for compounds containing donor substituents in position 6, substantial bathochromic shifts (comparable to analogous coumarins) of both absorption as well as fluorescence transitions are obtained. High absorption intensities and quantum yields are found for 7-donor substituted isomers. Semiempirical molecular orbital calculations (AMI for structures, ZINDO for electronic transition energies) prove to be a suitable tool for the prediction of absorption and fluorescence properties of these compounds. Ab initio and density functional calculations establish the lactam form as the dominant tautomer of the parent quinolin-2(1H)-one.