442-33-1

Usage

InChI:InChI=1/C20H25NO2/c1-21-17(12-10-16-6-4-5-7-18(16)21)11-8-15-9-13-19(22-2)20(14-15)23-3/h4-7,9,13-14,17H,8,10-12H2,1-3H3

Upstream product

• 104967-54-6 2-(3,4-dimethoxy-β-phenethyl)-1,2,3,4-tetrahydroquinoline 
• 74-88-4 methyl iodide 
• 75903-25-2 2-(3',4'-dimethoxystyryl)quinoline 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 1200112-80-6 methyl (2E)-5-(3,4-dimethoxyphenyl)-2-pentenoate 
• 1200112-82-8 (2E)-5-(3,4-dimethoxyphenyl)-2-penten-1-ol 
• 6380-23-0 3,4-dimethoxystyrene 
• 1360807-88-0 (-)-N-{(1S)-1-[2-(3,4-dimethoxyphenyl)ethyl]prop-2-en-1-yl}-2-iodoaniline 
• 1360807-86-8 (2E)-5-(3,4-dimethoxyphenyl)pent-2-en-1-yl methyl carbonate 
• 15115-58-9 3-(2-bromophenyl)propionic acid 
• 50-00-0 formaldehyd 
• 52221-92-8 3-(2-bromo-phenyl)-propan-1-ol 
• 107408-16-2 3-(o-bromophenyl)propanal 
• 91-22-5 quinoline 

Relevant academic research and scientific papers

A convergent approach towards the synthesis of the 2-alkyl-substituted tetrahydroquinoline alkaloid (?)-cuspareine

A convergent approach towards the synthesis of the 2-alkyl-substituted tetrahydroquinoline alkaloid (?)-cuspareine via enantiospecific construction of the (R)-benzyl 2-formyl-3,4-dihydroquinoline-1(2H)-carboxylate. We have achieved an efficient enantiospe

A highly enantioselective Bronsted acid catalyzed cascade reaction: Organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids

(Chemical Equation Presented) A categorical success: A Bronsted acid catalyzed cascade transfer hydrogenation provides direct access to 2-aryl- and 2-alkyl-substituted tetrahydroquinolines with excellent enantioselectivities under mild conditions and usin

Enantioselective Copper-Catalyzed Quinoline Alkynylation

A highly enantioselective copper-catalyzed alkynylation of quinolinium salts is reported. The reaction employs StackPhos, a newly developed imidazole-based chiral biaryl P,N ligand, and copper bromide to effect a three-component reaction between a quinoline, a terminal alkyne, and ethyl chloroformate. Under the reaction conditions, the desired products are delivered in high yields with ee values of up to 98 %. The transformation tolerates a wide range of functional groups with respect to both the alkyne and the quinoline starting materials and the products are easily transformed into useful synthons. Efficient, enantioselective syntheses of the tetrahydroquinoline alkaloids (+)-galipinine, (+)-angustureine, and (-)-cuspareine are reported.

Asymmetric total syntheses of (-)-Angustureine and (-)-cuspareine via rhodium-catalyzed hydroamination

Concise syntheses of the Hancock alkaloids (-)-Angustureine and (-)-cuspareine are presented, applying and refining a recently developed rhodium-catalyzed hydroamination for the stereoselective construction of the chiral secondary amine. Furthermore, the

Enantioselective synthesis of tetrahydroquinoline alkaloids (-)-angustureine and (-)-cuspareine from chiral tert-butanesulfinyl imines

The addition of a Grignard reagent to both enantiomeric N-tert-butanesulfinyl imines derived from 3-(2-bromophenyl)propanal 8 proceeded with high diastereoselectivity. The resulting sulfinamides 9 and 12 were easily transformed into tetrahydroquinoline alkaloids (-)-angustureine (4) and (-)-cuspareine (5) after three steps: N-desulfinylation, intramolecular N-arylation and N-methylation.

Cu(I)-Catalyzed Alkynylation of Quinolones

Herein we report the first alkynylation of quinolones with terminal alkynes under mild reaction conditions. The reaction is catalyzed by Cu(I) salts in the presence of a Lewis acid, which is essential for the reactivity of the system. The enantioselective version of this transformation has also been explored, and the methodology has been applied in the synthesis of the enantioenriched tetrahydroquinoline alkaloid cuspareine.

Manganese catalyzed C-alkylation of methylN-heteroarenes with primary alcohols

C-Alkylations of nine different classes of methyl-substitutedN-heteroarenes, including quinolines, quinoxalines, benzimidazoles, benzoxazoles, pyrazines, pyrimidines, pyridazines, pyridines, and triazines are disclosed. A bench stable earth-abundant Mn(i)-complex catalyzed the chemoselective hydrogen-transfer reaction utilizing a diverse range of primary alcohols as the non-fossil fuel-derived carbon source. The diversifiedN-heteroarenes (41 examples) were isolated in high yields and selectivities. Water is produced as the sole byproduct, making the protocol environmentally benign.

Deaminative Olefination of Methyl N-Heteroarenes by an Amine Oxidase Inspired Catalyst

We explored the bioinspired o-quinone cofactor catalyzed aerobic primary amine dehydrogenation for a cascade olefination reaction with nine different methyl N-heteroarenes, including pyrimidines, pyrazines, pyridines, quinolines, quinoxolines, benzimidazoles, benzoxazoles, benzthiazoles, and triazines. An o-quinone catalyst phd (1,10-phenanthroline-5,6-dione) combined with a Br?nsted acid catalyzed the reaction. N-Heteroaryl stilbenoids were synthesized in high yields and (E)-selectivities under mild conditions using oxygen (1 atm) as the sole oxidant without needing transition-metal salt, ligand, stoichiometric base, or oxidant.

Boric acid catalyzed chemoselective reduction of quinolines

Boric acid promoted transfer hydrogenation of substituted quinolines to synthetically versatile 1,2,3,4-tetrahydroquinolines (1,2,3,4-THQs) was described under mild reaction conditions using a Hantzsch ester as a mild organic hydrogen source. This methodology is practical and efficient, where isolated yields are excellent and reducible functional groups are well tolerated in the N-heteroarene moiety. The reaction parameters and tentative mechanistic pathways are demonstrated by various control experiments and NMR studies. The present work can also be scaled up to obtain gram quantities and the utility of the developed process is illustrated by the transformation of 1,2,3,4-THQs into a series of biologically important molecules including the antiarrhythmic drug nicainoprol.

Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N -propargylanilines with diverse carbon pronucleophiles: Facile access to functionalized tetrahydroquinolines

Zinc(ii)-catalyzed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N-propargylanilines with two types of carbon pronucleophiles (nitromethane as a sp3 carbon pronucleophile and phenylacetylenes as sp carbon pronucleophiles) proceeded to give the 2-substituted tetrahydroquinolines in good yields with 100percent atomic utilization without any additional external oxidants.