23432-40-8

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 2772, 1984 DOI: 10.1021/jo00189a025

InChI:InChI=1/C10H9NO/c1-7-2-3-9-8(6-7)10(12)4-5-11-9/h2-6H,1H3,(H,11,12)

Upstream product

• 35973-18-3 4-hydroxy-6-methyl-quinoline-3-carboxylic acid 
• 29289-13-2 2-iodo-4-methylaniline 
• 141-82-2 malonic acid 
• 106-49-0 p-toluidine 
• 122-51-0 orthoformic acid triethyl ester 
• 25428-06-2 2-amino-5-methyl-acetophenone 
• 109-94-4 formic acid ethyl ester 
• 624-31-7 4-tolyl iodide 
• 19056-84-9 diethyl 2-[(p-tolylamino)methylidene]malonate 
• 79607-24-2 6-methyl-4-carbonylquinoline-3-carboxylic acid ethyl ester 
• 2033-24-1 cycl-isopropylidene malonate 
• 107-31-3 Methyl formate 
• 38560-27-9 N-(4-methylphenyl)azetidin-2-one 
• 36054-00-9 6-methyl-2,3-dihydroquinolin-4(1H)-one 

Downstream Products

• 18436-71-0 4-chloro-6-methylquinoline 
• 91-62-3 6-methylquinoline 
• 325856-06-2 1,6-dimethylquinolin-4(1H)-one 
• 1283075-21-7 C₁₈H₁₅NO₃ 
• 1082748-37-5 C₁₀H₁₁N₃ 
• 1621082-95-8 4-methyl-N-(4-methyl-2-{1-[(4-methylphenyl)sulfonyl]-1Hpyrazol-3-yl}phenyl)benzenesulfonamide 

Relevant academic research and scientific papers

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.

Development of novel quinoline-based sulfonamides as selective cancer-associated carbonic anhydrase isoform ix inhibitors

A new series of quinoline-based benzenesulfonamides (QBS) were developed as potential carbonic anhydrase inhibitors (CAIs). The target QBS CAIs is based on the 4-anilinoquinoline scaffold where the primary sulphonamide functionality was grafted at C4 of t

Copper-Catalyzed Chemoselective Cyclization Reaction of 2-Isocyanoacetophenone: Synthesis of 4-Hydroxyquinoline Compounds

A copper-catalyzed intramolecular cyclization reaction of 2-isocyanoacetophenone derivatives to afford 4-hydroxyquinolines chemoselectively is described. The transformation proceeds through enol tautomerism and a subsequent C-C bond formation. Compared to previous methods, this study provides a new protocol for the construction of 4-hydroxyquinoline compounds from functionalized isocyanides under mild conditions.

Cobalt(III)- and Rhodium(III)-Catalyzed C-H Amidation and Synthesis of 4-Quinolones: C-H Activation Assisted by Weakly Coordinating and Functionalizable Enaminone

Cobalt(III) and rhodium(III) catalysts exhibited complementary scope in C-H amidation of aryl enaminones. The amidation reactions proceeded with broad scope under the assistance of a weakly coordinating and bifunctional enaminone directing group. The electrophilicity of the enaminone group can be further utilized in subsequent hydrolysis-cyclization reactions to afford NH 4-quinolones in telescoping reactions.

Synthesis of bridged benzazocines and benzoxocines by a titanium-catalyzed double-reductive umpolung strategy

A sequence of two titanium(III)-catalyzed reductive umpolung reactions is reported that allows the rapid construction of benzazo- and benzoxozine building blocks. The first step is a reductive cross-coupling of quinolones or chromones with Michael acceptors. This reaction proceeds with complete syn-selectivity for the quinolone functionalization while the anti-diastereomers are obtained as the major products from chromones. With different reaction conditions, the stereochemical outcome can be altered to afford the syn-chromanone products as well. A subsequent reductive ketyl radical cyclization forges the tricyclic title compounds in good yields. A stereochemical model explaining the observed stereoselectivities is provided and the product configurations were unambiguously verified by X-ray analyses and 2D NMR spectroscopic experiments.

Further studies on bis-charged tetraazacyclophanes as potent inhibitors of small conductance Ca2+-activated K+ channels

Previously, quinolinium-based tetraazacyclophanes, such as UCL 1684 and UCL 1848, have been shown to be extraordinarily sensitive to changes in chemical structure (especially to the size of the cyclophane system) with respect to activity as potent non-peptidic blockers of the small conductance Ca 2+-activated K+ ion channels (SKCa). The present work has sought to optimize the structure of the linking chains in UCL 1848. We report the synthesis and SKCa channel-blocking activity of 29 analogues of UCL 1848 in which the central CH2 of UCL 1848 is replaced by other groups X or Y = O, S, CF2, CO, CHOH, CC, CHCH, CHMe to explore whether subtle changes in bond length or flexibility can improve potency still further. The possibility of improving potency by introducing ring substituents has also been explored by synthesizing and testing 25 analogues of UCL 1684 and UCL 1848 with substituents (NO2, NH2, CF 3, F, Cl, CH3, OCH3, OCF3, OH) in the 5, 6 or 7 positions of the aminoquinolinium rings. As in our earlier work, each compound was assayed for inhibition of the afterhyperpolarization (AHP) in rat sympathetic neurons, an action mediated by the SK3 subtype of the SK Ca channel. One of the new compounds (39, R7 = Cl, UCL 2053) is twice as potent as UCL 1848 and UCL 1684: seven are comparable in activity.

Synthesis of 2,3-dihydro-4(1H)-quinolones and the corresponding 4(1H)-quinolones via low-temperature fries rearrangement of N-arylazetidin-2- ones

N-Arylazetidin-2-ones of the general form 1, which are readily prepared by GoldbergBuchwald-type copper-catalyzed coupling of N-unsubstituted azetidin-2-ones with the relevant aryl halide or using Mitsunobu cyclization processes, undergo smooth Fries-rearrangement in triflic acid at 018°C to give the isomeric 2,3-dihydro-4(1H)-quinolones (2). Dehydrogenation of the latter compounds using 10% Pd on C in 1.0M aqueous sodium hydroxide/propan-2-ol mixtures at ca. 82°C provides the corresponding 4(1H)-quinolones (3).

Direct C-3-alkenylation of quinolones via palladium-catalyzed C-H functionalization

An unprecedented C-3-alkenylation of quinolones was reported through palladium-catalyzed C-H functionalization with 1% catalyst loading. This method provides an efficient route to a variety of new quinolone derivatives.

Gas-phase pyrolysis in organic synthesis: Rapid green synthesis of 4-quinolinones

Gas-phase pyrolysis of aminomethylene Meldrum's acid derivatives gave quinolinones and/or amines depending on the nature of arylamino moiety. Effect of substituent on reaction rate and nature of pyrolysis products supports the suggested intramolecular nucleophilic substitution reaction via initially formed keteneamine intermediate. Georg Thieme Verlag Stuttgart.

Preparation of quinoline hexose analogs as novel chloroquine-resistant malaria treatments (1). Synthesis of 4-hydroxyquinoline-β-glucosides

Quinoline hexose analogs are expected to be useful as novel agents for treatment of chloroquine-resistant malaria. Here, we report preparation of 4-hydroxy quinoline-β-glucosides from anilines in 4 steps.