53761-50-5

Usage

Type of compound

Heterocyclic

Structure

Contains a quinoline ring with an ethyl substituent at the 1-position

Physical state

Yellow liquid at room temperature

Usage

Commonly used in the synthesis of various pharmaceuticals and agrochemicals

Potential applications

Building block for the development of new materials with specific properties

Medicinal chemistry interest

Studied for its potential antibacterial and antifungal properties

Industries of relevance

Pharmaceutical and materials science

InChI:InChI=1/C11H11NO/c1-2-12-10-6-4-3-5-9(10)7-8-11(12)13/h3-8H,2H2,1H3

Upstream product

• 109322-46-5 1-vinyl-quinolin-2(1H)-one 
• 634-35-5 N-ethylquinolinium iodide 
• 46185-83-5 2-ethoxyquinoline 
• 59-31-4 2-quinolone 
• 75-03-6 ethyl iodide 
• 91-22-5 quinoline 
• 54337-10-9 p-N,N-diethylaminobenzaldehyde 
• 69788-01-8 1-Ethyl-1,2,3,4-tetrahydro-2(1H)-quinolinone 

Relevant academic research and scientific papers

Redox-Triggered Switchable Synthesis of 3,4-Dihydroquinolin-2(1 H)-one Derivatives via Hydride Transfer/ N-Dealkylation/ N-Acylation

The switchable synthesis of 3-non, 3-mono, 3,3′-disubstituted 3,4-dihydroquinolin-2(1H)-ones was developed through a redox-neutral hydride-transfer/N-dealkylation/N-acylation strategy from o-aminobenzaldehyde with 4-hydroxycoumarin, and Meldrum's acid, respectively. The unprecedented strategy for the synthesis of 3,3′-highly functionalized 3,4-dihydroquinolin-2(1H)-one has been realized with the in situ utilization of the released HCHO via the o-QM involved Michael addition. In addition, the synthetic utility of this protocol has been well illustrated via concise synthesis of CYP11B2 inhibitor.

Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis

The value of catalytic dehydrogenation of aliphatics (CDA) in organic synthesis has remained largely underexplored. Known homogeneous CDA systems often require the use of sacrificial hydrogen acceptors (or oxidants), precious metal catalysts, and harsh reaction conditions, thus limiting most existing methods to dehydrogenation of non- or low-functionalized alkanes. Here we describe a visible-light-driven, dual-catalyst system consisting of inexpensive organophotoredox and base-metal catalysts for room-temperature, acceptorless-CDA (Al-CDA). Initiated by photoexited 2-chloroanthraquinone, the process involves H atom transfer (HAT) of aliphatics to form alkyl radicals, which then react with cobaloxime to produce olefins and H2. This operationally simple method enables direct dehydrogenation of readily available chemical feedstocks to diversely functionalized olefins. For example, we demonstrate, for the first time, the oxidant-free desaturation of thioethers and amides to alkenyl sulfides and enamides, respectively. Moreover, the system's exceptional site selectivity and functional group tolerance are illustrated by late-stage dehydrogenation and synthesis of 14 biologically relevant molecules and pharmaceutical ingredients. Mechanistic studies have revealed a dual HAT process and provided insights into the origin of reactivity and site selectivity.

An organocatalyst bound α-aminoalkyl radical intermediate for controlled aerobic oxidation of iminium ions

A catalyst bound α-aminoalkyl radical intermediate from iminium is developed to control its formation and reactivity with aerobic oxygen. The influence of the catalyst was demonstrated via the ease of radical intermediate formation and its subsequent reactivity, including the first catalyst-controlled enantioselective aerobic oxidation with a chiral phosphite catalyst.

QUINOLONES AS INHIBITORS OF CLASS IV BROMODOMAIN PROTEINS

The present invention provides compounds of formula (I) as described herein and pharmaceutically acceptable salts, hydrates and solvates thereof for use in medicine, for example in the treatment of acute myeloid leukaemia:

On the thermally induced rearrangement of 2-alkoxypyridines to N-alkylpyridones

Analogues of 2-methoxypyridine undergo rearrangement to N-methylpyridones under flash vacuum pyrolysis (FVP) conditions. Ethoxy derivatives undergo competitive ethyl migration and elimination of ethylene. Analogues of 4-methoxypyridine do not undergo rearrangement under FVP conditions, but demethylation on silica may occur. The ease of rearrangement follows the basicity of the alkoxyhetarene to some extent. The vapour-phase rearrangements have been contrasted to condensed-phase pyrolyses. and a four-centre transition state for the former is supported by computation. The rearrangement allows structural assignment to the two products from the reaction of 2,4-dichloroquinoline with pyrrolidine.

Synthesis of 3,4-dihydroisoquinolines, 2-alkyl(acyl)-1(2H)-3,4-dihydroisoquinolinones, 2-alkyl-1(2H)-isoquinolinones and 1-alkyl-2(2H)-quinolinones by oxidation with potassium permanganate

Synthesis of 3,4-dihydroisoquinolines 2, 2-alkyl- 6 and 2-acyl-3,4-dihydro-1(2H)-isoquinolinones 9, 2-alkyl-1(2H)-isoquinolinones 14, N-alkyl-3,4-dihydro-2(2H)-quinolinones 16 and N-alkyl-2(2H)-quinolinones 19 by oxidation of 1,2,3,4-tetrahydroisoquinolines 1, N-alkyl (acyl)iminium salts of 3,4-dihydroisoquinolines 5,8 and isoquinoline 13 as well as of N-alkyl ammonium salts of tetrahydroquinoline 15 and quinoline 18 with potassium permanganate is described.

5-lipoxygenase inhibitors quinoxalinyl derivatives

The invention concerns a heterocyclic derivative of the formula I STR1 wherein Q is an optionally substituted quinoxalinyl or a hydrogenated derivative thereof X1 is oxy, thio, sulphinyl, sulphonyl or imino; Ar is phenylene which may optionally bear one or two substituents or Ar is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms; R1 is (1-6C)alkyl, (3-6C)alkenyl or (3-6C)alkynyl; and R2 and R3 together form a group of the formula --A2 --X2 --A3 -- which, together with the carbon atom to which A2 and A3 are attached, defines a ring having 4 to 7 ring atoms, wherein A2 and A3, which may be the same or different, each is (1-4C)alkylene and X2 is oxy, thio, sulphinyl, sulphonyl or imino; or a pharmaceutically-acceptable salt thereof. The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.

5-LIPOXYGENASE INHIBITORS QUINOLINE OR ISOQUINOLINE DERIVATIVES

The invention concerns a heterocyclic derivative of the formula I wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms; X1 is oxy, thio, sulphinyl, sulphonyl or imino; Ar is phenylene which may optionally bear one or two substituents or Ar is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms; R1 is (1-6C)alkyl, (3-6C)alkenyl or (3-6C)alkynyl; and R2 and R3 together form a group of the formula ?A2?X2?A3? which, together with the carbon atom to which A2 and A3 are attached, defines a ring having 4 to 7 ring atoms, wherein A2 and A3, which may be the same or different, each is (1-4C)alkylene and X2 is oxy, thio, sulphinyl, sulphonyl or imino; or a pharmaceutically-acceptable salt thereof. The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase

Heterocyclic derivatives

The invention concerns a heterocyclic derivative of the formula I wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;, X1 is oxy, thio, sulphinyl, sulphonyl or imino;, Ar is phenylene which may optionally bear one or two substituents or, Ar is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;, R1 is (1-6C)alkyl, (3-6C)alkenyl or (3-6C)alkynyl; and, R2 and R3 together form a group of the formula -A2-X2-A3- which, together with the carbon atom to which A2 and A3 are attached, defines a ring having 4 to 7 ring atoms, wherein A2 and A3, which may be the same or different, each is (1-4C)alkylene and X2 is oxy, thio, sulphinyl, sulphonyl or imino;, or a pharmaceutically-acceptable salt thereof. The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.

192. Azidinium-Salze 23.Mitteilung Photolyse heterocyclischer Azidinium-Salze

The photochemistry of some azidinium salts was investigated.Their photolysis led to a large variety of products whichh were isolated and identified.Reaction mechanisms involving singlet and triplet nitrene intermediates are discussed to explain the product formation.