30958-79-3

Usage

InChI:InChI=1/C11H10N2O/c1-7-6-10(11(12)14)13-9-5-3-2-4-8(7)9/h2-6H,1H3,(H2,12,14)

Upstream product

• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 77287-34-4 formamide 
• 563-41-7 semicarbazide hydrochloride 
• 33787-85-8 (4-methyl-quinolin-2-yl)-methanol 
• 471-47-6 oxamic acid 

Relevant academic research and scientific papers

Polar Effects in Free-Radical Reactions. Carbamoylation and α-N-Amidoalkylation of Heteroaromatic Bases by Amides and Hydroxylamine-O-sulfonic Acid.

The decomposition by Fe(II) salt of hydroxylamine-O-sulfonic acid (HSA) in the presence of formamide, alkylformamides, and N-alkylacetamides provides the amino radical cation *+NH3, which by hydrogen abstraction generates carbamoyl (*CON) and α-N-amidoalkyl (CON*C) radicals.Both kinds of radicals have a clear-cut nucleophilic character and selectively attack protonated heteroaromatic bases, such as 4-methylquinoline or quinoxaline, in the α-position or are oxidized by Fe(III) salts.Redox chain mechanisms are involved.The importance of the polar effects in the hydrogen abstraction, aromatic substitution, and oxidation by Fe(III) salt is discussed.

Redox-chain Decomposition of Hydroxylamine-O-sulphonic Acid. A Novel General Source of Nucleophilic Radicals for the Functionalization of Heteroaromatic Bases

Protonated heteroaromatic bases react with formamide, N,N-dimethylformamide, cyclic ethers, and methanol in the presence of hydroxylamine-O-sulphonic acid and catalytic amounts of an iron(II) salt to afford selective substitution by a redox chain process.

A novel and mild source of carboncentered radicals by iodosobenzene diacetate (IBDA) and sodium azide from alcohols, ethers, aldehydes, amides and alkyl iodides

A radical process for the thermal decomposition of IBDA in the presence of sodium azide; by this method, carbon centered radicals can be generated either by hydrogen abstraction from the solvent (an alcohol, an ether, an aldehyde or formamide) or by iodin

Silver-catalyzed direct C-H oxidative carbamoylation of quinolines with oxamic acids

A silver-catalyzed efficient and direct C-H carbamoylation of quinolines with oxamic acids to access carbamoylated quinolines has been developed through oxidative decarboxylation reaction. The reaction proceeds smoothly over a broad range of substrates wi

Metal-, Photocatalyst-, and Light-Free Direct C-H Acylation and Carbamoylation of Heterocycles

Direct C-H acylations and carbamoylations of heterocycles can now be readily achieved without requiring any conventional metal, photocatalyst, electrocatalysis, or light activation, thus significantly improving on sustainability, costs, toxicity, waste, and simplicity of the operational procedure. These mild conditions are also suitable for gram-scale reactions and late-stage functionalizations of complex molecules, including pharmaceuticals, N,N-ligands, and light-sensitive molecules.

Hydroxymethylation of Quinolines with Na2S2O8 by a Radical Pathway

Quinolines and isoquinolines were treated with Na2S2O8 in a mixture of methanol and water at 70 °C to form hydroxymethylated quinolines and isoquinolines in good to moderate yields, under transition-metal-free conditions. The formed hydroxymethyl group was smoothly converted into aldehyde, ester, amide, bromomethyl, (N,N-diethylamino)methyl, cyano, and tetrazole groups, in good yields.

Highly Regioselective Carbamoylation of Electron-Deficient Nitrogen Heteroarenes with Hydrazinecarboxamides

The use of hydrazinecarboxamides as a new class of carbamoylating agents has been established through the dehydrazinative Minisci reaction of electron-deficient nitrogen heteroarenes. A wide range of electron-deficient nitrogen heteroarenes, including isoquinoline, quinoline, pyridine, phenanthridine, quinoxaline, and phthalazine, underwent copper/acid-catalyzed oxidative carbamoylation with hydrazinecarboxamide hydrochlorides to afford structurally diverse nitrogen-heteroaryl carboxamides as single regioisomers in moderate to excellent yields. The functional group tolerance was substantially demonstrated in the direct carbamoylation of quinine obviating multistep sequences involving protecting groups and prefunctionalization of the heterocycle.

Sunlight induced functionalisation of some heterocyclic bases in the presence of polycrystalline TiO2

The functionalisation of various heterocyclic bases induced by sunlight is reported. The photoreaction occurred with higher yield in a liquid-solid heterogeneous system in the presence of polycrystalline TiO2 (anatase) than in a homogeneous system under the same experimental conditions.

A novel, selective free-radical carbamoylation of heteroaromatic bases by Ce(IV) oxidation of formamide, catalysed by N-hydroxyphthalimide

The Ce(IV)-NHPI system was used to generate a carbamoyl radical by oxidation of formamide; this nucleophilic radical has been successfully used in the carbamoylation of heteroaromatic bases.

POLAR EFFECTS IN FREE-RADICAL REACTIONS. NEW SYNTHETIC DEVELOPMENTS IN THE FUNCTIONALIZATION OF HETEROAROMATIC BASES BY NUCLEOPHILIC RADICALS

The synthetic interest of the direct substitution of protonated heteroaromatic bases by nucleophilic carbon-centered radicals is furtheron developed by the following new achievements: i) utilization of the redox system N(+)H3OH/Ti(III) in several solvents; ii) utilization of benzoyl peroxide in alcohols; iii) carbamoylation by HCONH2 and H2O2 in the presence of catalytic amounts of Fe(II).These systems allow to obtain either substitution till now tried without success or reactions of industrial interest.Polar effects play a dominat role in determining reactivity, selectivity and synthetic applications; in particular the role of the strongly nucleophilic intermediate radicals of pyridinyl type in the rearomatization step is emphasized.