6560-83-4

Usage

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 6757, 1990 DOI: 10.1016/S0040-4039(00)97163-6Chemical and Pharmaceutical Bulletin, 30, p. 1731, 1982 DOI: 10.1248/cpb.30.1731

InChI:InChI=1/C9H6IN/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H

Upstream product

• 79476-04-3 (2-quinolyl)trimethylstannane 
• 109586-44-9 trifluoromethanesulfonic acid quinolin-2-yl ester 
• 59-31-4 2-hydroxyquinoline 
• 612-62-4 2-Chloroquinoline 
• 10034-85-2 hydrogen iodide 
• 91-22-5 quinoline 

Downstream Products

• 6294-65-1 2-pyridin-3-yl-quinoline 
• 1436-43-7 quinoline-2-carbonitrile 
• 1006889-89-9 7-methoxy-4-(3-phenylpiperidin-1-yl)-6-[(3-quinolin-2-ylprop-2-yn-1-yl)oxy]quinazoline 
• 91-22-5 quinoline 
• 83036-89-9 2-(1H-pyrrol-2-yl)quinoline 
• 129887-31-6 2-(1H-pyrrol-3-yl)quinoline 
• 18714-34-6 2-nitro-quinoline 
• 612-62-4 2-Chloroquinoline 
• 129887-30-5 2-(1-methylpyrrol-3-yl)quinoline 
• 83036-88-8 2-(1-methyl-2<1H>-pyrrolyl)quinoline 
• 143035-49-8 α-(4-chlorophenyl)-2-quinolineacetonitrile 
• 143035-51-2 α-(4-methoxyphenyl)-2-quinolineacetonitrile 
• 5100-57-2 ethyl 2-(2-quinolyl)acetate 
• 22297-12-7 α-(2-quinolyl)phenylacetonitrile 

Relevant academic research and scientific papers

Iodopyridines from bromo- and chloropyridines

Bromo- and chloropyridines may be converted to the corresponding iodopyridines by treatment with sodium iodide and acetyl chloride in acetonitrile.

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.

Probing the catalytic promiscuity of a regio- and stereospecific C-glycosyltransferase from Mangifera indica

The catalytic promiscuity of the novel benzophenone C-glycosyltransferase, MiCGT, which is involved in the biosynthesis of mangiferin from Mangifera indica, was explored. MiCGT exhibited a robust capability to regio- and stereospecific C-glycosylation of 35 structurally diverse druglike scaffolds and simple phenolics with UDP-glucose, and also formed O- and N-glycosides. Moreover, MiCGT was able to generate C-xylosides with UDP-xylose. The OGT-reversibility of MiCGT was also exploited to generate C-glucosides with simple sugar donor. Three aryl-C-glycosides exhibited potent SGLT2 inhibitory activities with IC50 values of 2.6×, 7.6×, and 7.6×10-7-M, respectively. These findings demonstrate for the first time the significant potential of an enzymatic approach to diversification through C-glycosidation of bioactive natural and unnatural products in drug discovery. C-glycodiversification: MiCGT, as the first benzophenone C-glycosyltransferase (CGT) from Mangifera indica, showed robust regio- and stereospecific C-glycosylation activity for 35 structurally diverse acceptors with UDP-glucose or xylose. The aryl-C-glycoside 1 exhibited potent antidiabetic activity toward SGLT2.

Synthesis of 7,7′-Dihydroxy-8,8′-biquinolyl (azaBINOL) via Pd-catalyzed directed double C-H functionalization of 8,8′-biquinolyl: Emergence of an atropos from a tropos state

7,7′-Dihydroxy-8,8′-biquinolyl (azaBINOL) was prepared from 2-chloroaniline in four steps: (1) the Skraup reaction, (2) Ni-catalyzed reductive coupling of 8-chloroquinoline, (3) Pd(II)-catalyzed double C-H functionalization of 8,8′-biquinolyl mediated by

AMINO-HETEROCYCLIC COMPOUNDS

The invention provides PDE9-inhibiting compounds of Formula (I), and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, A, and n are as defined herein. Pharmaceutical compositions containing the compounds of Formula I, and uses thereof in treating neurodegenerative and cognitive disorders, such as Alzheimer's disease and schizophrenia, are also provided.

Microwave-assisted trans-halogenation reactions of various chloro-, bromo-, trifluoromethanesulfonyloxy- and nonafluorobutanesulfonyloxy-substituted quinolines, isoquinolines, and pyridines leading to the corresponding iodinated heterocycles

(Chemical Equation Presented) Microwave irradiation of certain chloro-, bromo-, trifluoromethanesulfonyloxy- and nonafluorobutanesulfonyloxy-substituted quinolines in the presence of acetic anhydride and sodium iodide leads, via a trans-halogenation process, to the corresponding iodides in high yield. Related conversions involving pyridines and isoquinolines can also be achieved under similar conditions.

Aryl pyrrolidinyl and piperidinyl ketone derivatives and uses thereof

Aryl and heteroaryl ketone compounds substituted with pyrrolidines and piperidines, that modulate serotonin norepinephrine and/or dopamine neurotransmission. Also provided are pharmaceutical compositions, methods of using, and methods of preparing the com

One-pot iodination of hydroxypyridines

(Chemical Equation Presented) A one-pot, high-yielding iodination of hydroxypyridines and hydroxyquinolines is described. The iodination proceeds under mild conditions, and the products are obtained in high yield without the need for chromatographic purif

Heteroaryl pyrrolidinyl and piperidinyl ketone derivatives and uses thereof

Compounds of the formula: or pharmaceutically acceptable salts thereof, wherein m, n, Ar, R1, R2, Ra and Rb are defined herein. Also provided are pharmaceutical compositions, methods of using, and methods of pre

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.