3033-80-5

Usage

Uses

Used in Pharmaceutical Development:
8-METHOXY-2-METHYLQUINOLINE is used as a chemical framework for the development of various therapeutic agents, particularly in the pharmaceutical industry. Its relevance in this field stems from the fact that quinolines are a common structural component in the design of several drugs, including anticancer, antimalarial, and antibiotic medications.
Used in Anticancer Drug Development:
8-METHOXY-2-METHYLQUINOLINE is used as a key component in the synthesis of anticancer drugs. Its presence in the molecular structure of these drugs allows for the modulation of various oncological signaling pathways, which can lead to the inhibition of tumor growth and progression.
Used in Antimalarial Drug Development:
8-METHOXY-2-METHYLQUINOLINE is used as a building block in the creation of antimalarial drugs. The incorporation of 8-METHOXY-2-METHYLQUINOLINE into the molecular structure of antimalarial medications can contribute to the effectiveness of these drugs in treating malaria.
Used in Antibiotic Development:
8-METHOXY-2-METHYLQUINOLINE is used as a structural element in the formulation of antibiotics. Its presence in the molecular makeup of these drugs can enhance their ability to combat bacterial infections and contribute to the overall effectiveness of the antibiotic.

InChI:InChI=1/C11H11NO/c1-8-6-7-9-4-3-5-10(13-2)11(9)12-8/h3-7H,1-2H3

Upstream product

• 79204-83-4 4-(3-methoxyphenyl)-2-butanone oxime 
• 191484-58-9 (E)-4-(3-methoxyphenyl)butan-2-one oxime 
• 90-04-0 2-methoxy-phenylamine 
• 109-92-2 ethyl vinyl ether 

Downstream Products

• 78224-64-3 (E)-8-methoxy-2-styrylquinoline 
• 103854-64-4 8-methoxy-2-quinolinecarboxaldehyde 
• 103862-55-1 5-bromo-8-methoxy-2-methylquinoline 
• 21141-35-5 8-methoxyquinoline-2-carboxylic acid 
• 852402-76-7 (S)-8-methoxyquinoline-2-carboxylic acid (1-phenylethyl)amide 
• 852402-86-9 (2S,3'S)-8-methoxy-1,2,3,4-tetrahydroquinoline-2-carboxylic acid (1-phenylethyl)amide 
• 852402-81-4 (2R,3'S)-8-methoxy-1,2,3,4-tetrahydroquinoline-2-carboxylic acid (1-phenylethyl)amide 
• 852403-02-2 (4aR,1'S)-10-methoxy-3-(1-phenylethyl)-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline 
• 852403-07-7 (4aS,1'S)-10-methoxy-3-(1-phenylethyl)-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline 
• 852402-92-7 (4aR,1'S)-10-methoxy-3-(1-phenylethyl)-2,3,4,4a,5,6-hexahydropyrazino[1,2-a]quinolin-1-one 
• 852402-97-2 (4aS,1'S)-10-methoxy-3-(1-phenylethyl)-2,3,4,4a,5,6-hexahydropyrazino[1,2-a]quinolin-1-one 

Relevant academic research and scientific papers

Assembly of substituted 2-alkylquinolines by a sequential palladium-catalyzed Ci-N and Ci-C bond formation

Diversity: A range of substituted 2-alkylquinolines can be prepared in a general and efficient synthetic approach that employs mild reaction conditions (see scheme). The synthesis is based on a sequential palladium-catalyzed Ci-N and Ci-C bond formation, followed by palladium-catalyzed aromatization, and results in the formation of the desired compounds in one step. Copyright

Synthesis of Quinolines and 2H-Dihydropyrroles by Nucleophilic Substitution at the Nitrogen Atom of Oxime Derivatives

Isomerization of oxime derivatives was researched in detail to find out the methods for the syn-anti isomerization of O-substituted oximes. Based on these findings were developed simple methods for the preparation of aza-heterocycles from both stereoisomers of oximes. Quinolines were synthesized from β-aryl ketone oximes by treatment with trifluoroacetic anhydride and 4-chloranil. γ,δ-Unsaturated O-methoxyacetyloximes were transformed to 2H-dihydropyrroles by reaction with methoxy-acetic acid.

Transformation of oximes of phenetyl ketone derivatives to quinolines and azaspirotrienones catalyzed by tetrabutylammonium perrhenate and trifluoromethanesulfonic acid

Phenethyl ketone oximes are converted to quinolines by the treatment with tetrabutylammonium perrhenate, trifluoromethanesulfonic acid, and chloranil in refluxing 1,2-dichloroethane. Azaspirotrienones can be synthesized from p-hydroxyphenethyl or 3-(p-hydroxyphenyl)propyl ketone oximes by applying the above method. Thus prepared azaspirotrienones are converted to quinolines by acid treatment.

Synthesis of Quinolines via Intramolecular Cyclization of Benzylacetone Oxime Derivatives Catalyzed with Tetrabutylammonium Perrhenate(VII) and Trifluoromethanesulfonic Acid

Intramolecular cyclization reaction on the nitrogen atom of benzylacetone oxime derivatives, which have electron donating group(s) on the phenyl group, proceeds by treatment with tetrabutylammonium perrhenate, trifluoromethanesulfonic acid, and 4-chloranil in refluxing 1,2-dichloroethane to afford quinoline derivatives in good yield.