27104-55-8

Upstream product

• 5470-96-2 quinoline 2-carbaldehyde 
• 91-22-5 quinoline 
• 100-52-7 benzaldehyde 
• 1074-12-0 phenylglyoxal hydrate 
• 52670-38-9 2-ethynylaniline 
• 1613-37-2 Quinoline N-oxide 
• 91-63-4 2-methylquinoline 
• 16576-25-3 2-benzoylquinoline 
• 2005-43-8 2-bromoquinoline 
• 612-62-4 2-Chloroquinoline 
• 98-86-2 acetophenone 
• 67-56-1 methanol 
• 93-10-7 quinoline-2-carboxylic acid 

Downstream Products

• 16576-25-3 2-benzoylquinoline 
• 1745-77-3 2-benzylquinoline 
• 1513327-00-8 2-(1-phenylethyl)quinoline 
• 132499-94-6 NPHQTS 
• 70391-44-5 2-[(2-morpholin-4-yl-ethoxy)-phenyl-methyl]-quinoline 

Relevant academic research and scientific papers

Copper(i)-catalyzed tandem synthesis of 2-acylquinolines from 2-ethynylanilines and glyoxals

An efficient one-step synthesis of 2-acylquinolines using a copper-catalyzed tandem reaction of 2-ethynylanilines with glyoxals in the presence of piperidine has been developed. This new protocol successfully avoids multi-step operation and the use of highly toxic cyanides required in traditional methods, and provides a practical tool for synthetic and pharmaceutical chemists. Various 2-acylquinolines are obtained with perfect regioselectivity in moderate to good yields (up to 86%). The potential synthetic utility of this method is exemplified by a large-scale experiment and synthetic transformation of the products.

From Pyridine- N-oxides to 2-Functionalized Pyridines through Pyridyl Phosphonium Salts: An Umpolung Strategy

The reactions of pyridine-N-oxides with Ph3P under the developed conditions provide an unprecedented route to (pyridine-2-yl)phosphonium salts. Upon activation with DABCO, these salts readily serve as functionalized 2-pyridyl nucleophile equivalents. This umpolung strategy allows for the selective C2 functionalization of the pyridine ring with electrophiles, avoiding the generation and use of unstable organometallic reagents. The protocol operates at ambient temperature and tolerates sensitive functional groups, enabling the synthesis of otherwise challenging compounds.

Photochemical C?H Hydroxyalkylation of Quinolines and Isoquinolines

We report herein a visible light-mediated C?H hydroxyalkylation of quinolines and isoquinolines that proceeds via a radical path. The process exploits the excited-state reactivity of 4-acyl-1,4-dihydropyridines, which can readily generate acyl radicals upon blue light absorption. By avoiding the need for external oxidants, this radical-generating strategy enables a departure from the classical, oxidative Minisci-type pattern and unlocks a unique reactivity, leading to hydroxyalkylated heteroarenes. Mechanistic investigations provide evidence that a radical-mediated spin-center shift is the key step of the process. The method's mild reaction conditions and high functional group tolerance accounted for the late-stage functionalization of active pharmaceutical ingredients and natural products.

The Diverse One-Pot Reactions of 2-Quinolylzincates: Homologation, Electrophilic Trapping, Hydroxylation, and Arylation Reactions

2-Quinolylzincates were efficiently produced from the regioselective metalation reactions of quinoline with various organozincates as key intermediates. The four different types of title reactions of these intermediates under the presented reaction conditions allowed for the facile formation of the corresponding C-2 functionalized quinolines, which are not successfully accessed through typical zincation methods.

Partial hydrogenation of substituted pyridines and quinolines: A crucial role of the reaction conditions

Hydrogenation of pyridyl and quinolyl compounds 2-substituted with a carbonyl group (1a-c and 2b,c) using PtO2 and 1 equiv. of HCl (conditions A) provides clean and total formation of the desired amino alcohol (hydrogenation of the heterocyclic ring and of the carbonyl) while under conditions B1 and/or B2 (concentrated HCl or pure CF 3CO2H) the heterocyclic ring remains untouched and other aromatic parts are hydrogenated providing complex mixtures. When the heterocyclic ring is substituted by an alkyl group (quinaldine 3) conditions A provide mixtures while under conditions B2 (pure CF 3CO2H) the benzene ring is cleanly hydrogenated leading to a pure product.

Tributylmagnesium ate complex-mediated bromine-magnesium exchange of bromoquinolines: A convenient access to functionalized quinolines

2-, 3- and 4-bromoquinolines were converted to the corresponding lithium tri(quinolyl)magnesates at -10°C by treatment with Bu3MgLi in THF or toluene. The resulting organomagnesium derivatives were quenched by various electrophiles to afford functionalized quinolines.

Synthesis and reactivity of lithium tri(quinolinyl)magnesates

2-, 3- and 4-Bromoquinolines were converted to the corresponding lithium tri(quinolinyl)magnesates at -10°C when exposed to Bu3MgLi in THF. The resulting organomagnesium derivatives were quenched with various electrophiles or involved in metal-catalyzed coupling reactions with heteroaryl halides to afford functionalized quinolines.

Naphthalene-catalysed lithiation of chlorinated nitrogenated aromatic heterocycles and reaction with electrophiles

Naphthalene catalysed reductive lithiation of various chloroazines (1, 7, 10, 13) in the presence of different electrophiles yields, after hydrolysis, the expected functionalised heterocycles with one (2, 8), two (11, 14a-d) and three nitrogen atoms in the ring (14e,f). This methodology allowed us to trap in situ the lithium imine derived from the reaction of 2- pyridyllithium with benzonitrile, by reaction with a Grignard reagent in the presence of titanium alkoxides. 2,4-Dimethoxypyrimidines (14a,c,d) are demethylated under acidic conditions to give the corresponding uracil derivatives 16. (C) 2000 Elsevier Science Ltd.

Aggregative activation in heterocyclic chemistry. Part 5. Lithiation of pyridine and quinoline with the complex base BuLi·Me2N(CH2)2OLi (BuLi·LiDMAE)

It is shown that the complex base BuLi·LiDMAE reacts with pyridine to give metallated species which, after trapping by electrophiles, lead to 2-substituted pyridines in good to excellent yields. The same reactions have been less successfully performed with quinoline.

Synthesis and Chromogenic Properties of Some Water-Soluble 5-Nitro-2-pyridylhydrazones

Four new water-soluble hydrazones, α-(5-nitro-2-pyridyl)hydrazono-α-(2-quinolyl)-3-toluenesulfonic acid, α-(5-nitro-2-pyridyl)hydrazono-α-(2-thiazolyl)-3-toluenesulfonic acid, α-(2-benzothiazolyl)-α-(5-nitro-2-pyridyl)hydrazono-3-toluenesulfonic acid, and α-(2-benzimidazolyl)-α-(5-nitro-2-pyridyl)hydrazono-3-toluenesulfonic acid, were synthesized.Their proton dissociation constants were determined spectrophotometrically.The chromogenic properties of the synthesized hydrazones and their reactions with metal ions were investigated spectrophotometrically in detail.The results revealed that the synthesized hydrazones react with various metal ions including transition metal ions, especially with cadmium(II), nickel(II), and zinc(II) to form stable colored comoplexes with very large apparent molar absorptivities, so that their were found to be all very useful as highly sensitive spectrophotometric reagents.