22493-93-2

Upstream product

• 860719-98-8 2-sec-butyl-1-methyl-1,2-dihydro-quinoline 
• 91-22-5 quinoline 
• 598-30-1 sec.-butyllithium 
• 53317-06-9 B-sec-butyl-9-borabicyclo<3.3.1>nonane 
• 75164-10-2 2-lithioquinoline 
• 1113-78-6 tri(sec-butyl)borane 
• 5344-90-1 2-Aminobenzyl alcohol 
• 565-61-7 3-methyl-pentan-2-one 
• 3947-76-0 N-methylquinolinium iodide 
• 18936-17-9 2-methylbutanenitrile 
• 103-63-9 1-phenyl-2-bromoethane 

Relevant academic research and scientific papers

ZnMe2-Mediated, Direct Alkylation of Electron-Deficient N-Heteroarenes with 1,1-Diborylalkanes: Scope and Mechanism

The regioselective, direct alkylation of electron-deficient N-heteroarenes is, in principle, a powerful and efficient way of accessing alkylated N-heteroarenes that are important core structures of many biologically active compounds and pharmaceutical agents. Herein, we report a ZnMe2-promoted, direct C2- or C4-selective primary and secondary alkylation of pyridines and quinolines using 1,1-diborylalkanes as alkylation sources. While substituted pyridines and quinolines exclusively afford C2-alkylated products, simple pyridine delivers C4-alkylated pyridine with excellent regioselectivity. The reaction scope is remarkably broad, and a range of C2- or C4-alkylated electron-deficient N-heteroarenes are obtained in good yields. Experimental and computational mechanistic studies imply that ZnMe2 serves not only as an activator of 1,1-diborylalkanes to generate (α-borylalkyl)methylalkoxy zincate, which acts as a Lewis acid to bind to the nitrogen atom of the heterocycles and controls the regioselectivity, but also as an oxidant for rearomatizing the dihydro-N-heteroarene intermediates to release the product.

Preparation of 2-Arylquinolines from 2-Arylethyl Bromides and Aromatic Nitriles with Magnesium and N -Iodosuccinimide

Treatment of 2-arylethylmagnesium bromides, prepared from 2-arylethyl bromides and magnesium, with aromatic nitriles, followed by reaction with water and then with N -iodosuccinimide under irradiation with a tungsten lamp, gave the corresponding 2-arylquinolines in good to moderate yields under transition-metal-free conditions. 2-Alkylquinolines could be also obtained in moderate yields by the same procedure with 2-arylethyl bromides, magnesium, aliphatic nitriles bearing a secondary alkyl group, and N -iodosuccinimide.

A rhodium-catalyzed route for oxidative coupling and cyclization of 2-aminobenzyl alcohol with ketones leading to quinolines

2-Aminobenzyl alcohol undergoes oxidative cyclization with aryl(alkyl), alkyl(alkyl) and cyclic ketones in dioxane at 80° in the presence of a catalytic amount of RhCl(PPh3)3 along with KOH to afford the corresponding quinolines in good yields. The catalytic pathway seems to be proceeded via a sequence involving initial oxidation of 2-aminobenzyl alcohol to 2-aminobenzaldehyde by a rhodium catalyst, cross aldol reaction between 2-aminobenzaldehyde and ketones, and cyclodehydration.

Allenes. Part 49. 4-Amino-2-(1-hydroxyalkyl)quinolines from Phenylhydroxylamine and Allenic Nitriles

Allenic nitriles, when heated with phenylhydroxylamine in ethanol for 24 h, form the intermediate 2-alkylidene-4-amino-1,2-dihydro-1-hydroxyquinolines (4) which rearrange spontaneously by a 1,3-hydroxy shift to 4-amino-2-(1-hydroxyalkyl)quinolines.The 1-hydroxyquinoline intermediate (4) does not isomerise to 2-alkyl-4-aminoquinoline 1-oxide by a 1,4-proton shift as shown by an independent synthesis of the latter.Phenylpropynenitrile with phenylhydroxylamine gave 8percent of 4-amino-2-(2-hydroxyphenyl)quinoline (15).

REACTIONS OF TRIALKYL(2- or 4-QUINOLYL)BORATES

Reactions of trialkyl(2-quinolyl)borates and trialkyl(4-quinolyl)borates were investigated.