589-41-3

Usage

Uses

Used in Chemical Synthesis:
N-Hydroxyurethane is used as a reactant in the synthesis of molecules used for intermolecular Sharpless aminohydroxylation reactions, intermolecular ortho-C-H amidation of anilides, cinchona alkaloid-catalyzed asymmetric cycloaddition, and allylic arylation. Its involvement in these reactions contributes to the development of new compounds and molecules with potential applications in various industries.
Used in Drug Development:
As a metabolite of carcinogenic Urethane (U825300), N-Hydroxyurethane may have potential applications in drug development, particularly in the study of its metabolic pathways and the development of drugs targeting these pathways. Further research is needed to explore its potential uses in this field.

Biochem/physiol Actions

N-Hydroxyurethane causes the chromosomal fragmentation at millimolar concentrations and cell toxicity in cultured normal human leukocytes.

InChI:InChI=1/C3H7NO3/c1-2-7-3(5)4-6/h6H,2H2,1H3,(H,4,5)

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 105-58-8 Diethyl carbonate 
• 7803-49-8 hydroxylamine 
• 64-17-5 ethanol 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 51-79-6 urethane 
• 5555-72-6 N-benzyloxycarbamic acid ethyl ester 
• 1867-23-8 N-benzyloxy-N-benzylcarbamic acid ethyl ester 
• 54020-55-2 N-(ethoxycarbonyl)isoxazolidine 
• 4585-46-0 α--phenylessigsaeure 
• 13278-89-2 N-<5-chlor-2-nitro-phenoxy>-urethan 
• 15308-35-7 N-(3,4-Dichlor-benzyloxy)-carbamidsaeure-ethylester 
• 52245-10-0 N-Carboethoxy-O-2,4,6-trimethylbenzylhydroxylamin 
• 5555-70-4 N-(4-Chlor-benzyloxy)-carbaminsaeure-ethylester 
• 5553-48-0 N-(4-Methyl-benzyl)-N-(4-methyl-benzyloxy)-carbamidsaeure-ethylester 
• 13278-82-5 (p-nitrophenoxy)-carbamic acid, ethyl ester 
• 13435-87-5 N-<2-Nitro-phenoxy>-urethan 
• 13278-85-8 Ethyl-N-(2,6-dinitro-phenoxy)-carbamat 
• 68871-52-3 N--carbaminsaeure-ethylester 

Relevant academic research and scientific papers

An Effective Method for the Synthesis of 1,3-Dihydro-2H-indazoles via N-N Bond Formation

The [4+1] cycloaddition reaction of bifunctional amino reagents has been achieved with in situ formed aza-ortho-quinone methides. Specifically, N-(tosyloxy)carbamates were used as an N1 synthon and bifunctional amino reagents for this transformation, which provides a metal-free, catalyst-free, and oxidant-free strategy to form nitrogen-nitrogen bonds. (Figure presented.).

Synthesis of indoles from aroyloxycarbamates with alkynes: Via decarboxylation/cyclization

An efficient Pd-catalyzed decarboxylation/cyclization of aroyloxycarbamates to realize substituted indoles has been disclosed. Terminal alkynes as the coupling partners lead to site specific 2-substituted indoles through two pathways, while internal alkynes with aroyloxycarbamates can be transformed to 2,3-disubstituted indoles directly. This protocol is further demonstrated by the efficient synthesis of indoles as well as the success of employing inexpensive aryl acids as starting materials to construct C-N bonds by releasing CO2.

Synthesis of N-Oxyureas by Substitution and Cope-Type Hydroamination Reactions Using O-Isocyanate Precursors

Oxy-carbamate O-isocyanate precursors facilitate access to synthetically valuable N-oxyureas via substitution with amines. This work exploits the reactivity of suitable O-isocyanate precursors, identified by a thorough study highlighting the different reactivity of isocyanate masking groups. This led to bench-stable O-isocyanate precursors, offering improved versatility in the synthesis of N-oxyureas, and demonstrates the controlled reactivity of masked O-isocyanates. Suitable precursors also enabled the first example of Cope-type hydroamination of unsaturated hydroxyureas.

Regioselective Synthesis of 2-Vinylanilines Using O-aroyloxycarba-mates by Sequential Decarboxylation/Amination/Heck Reaction

A new sequential approach for 2-vinylanilines utilizing aryl carboxylic acids as stable, inexpensive and widely available arylating reagents is described. Employing a Pd-POVs catalyst system, this protocol is not only overcoming the restriction barrier of decarboxylative coupling to ortho-substituted substrates, but also provides site-special to create new C(sp2)-N and C(sp2)-C(sp2) bonds. Mechanistic experiments suggest the cleavage of C(sp2)-COOH gives priority to C(sp2)-X bond in this reaction.

Palladium-Catalyzed Decarboxylative Synthesis of Arylamines

A novel approach has been developed for the synthesis of arylamines via the palladium-catalyzed intramolecular decarboxylative coupling (IDC) of aroyloxycarbamates, obtained in situ by reacting aryl carboxylic acids with hydroxycarbamates. The reaction offers facile access to structurally diverse arylamines with the site-specific formation of the C(sp2)-N bond under mild conditions.

Iron(II)-catalyzed intermolecular amino-oxygenation of olefins through the N - O bond cleavage of functionalized hydroxylamines

An iron-catalyzed diastereoselective intermolecular olefin amino-oxygenation reaction is reported, which proceeds via an iron-nitrenoid generated by the N - O bond cleavage of a functionalized hydroxylamine. In this reaction, a bench-stable hydroxylamine derivative is used as the amination reagent and oxidant. This method tolerates a range of synthetically valuable substrates that have been all incompatible with existing amino-oxygenation methods. It can also provide amino alcohol derivatives with regio- and stereochemical arrays complementary to known amino-oxygenation methods.

Alkyl 4-chlorobenzoyloxycarbamates as highly effective nitrogen source reagents for the base-free, intermolecular aminohydroxylation reaction

Ethyl-(7), benzyl-(8), tert-butyl-(9), and fluorenylmethyl-4- chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effective under base-free reaction conditions. The scope and limitations of these methods have been explored using a variety of alkenes, among which, trans-cinnamates, in particular, proved to be good substrates.

IMPROVED AMINOHYDROXYLATION OF ALKENES

The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.

IMPROVED PROCESS FOR THE PREPARATION OF (±)-1-(1-BENZO[B]THIEN-2-YLETHYL)-1-HYDROXYUREA

The present invention relates to an improved process for the preparation of (±)-1-(I -Benzo[b]thien-2-ylethyl)-1-hydroxyurea compound of formula 1.

Synthesis and in vitro cytotoxic activity of N-2-(2-furyl)-2- (chlorobenzyloxyimino) ethyl ciprofloxacin derivatives

Quinolone are a class of potent broad-spectrum antibacterial drugs that target the bacterial type II DNA topoisomerases (DNA gyrase) and topoisomerase IV. In the present study, the synthesis and evaluation of cytotoxicity activity of a new series of N-pipearzinyl quinolones containing N-2-(furyl-2-yl)-2- (chlorobenzyloxyimino) ethyl moiety (6a-c) have been studied. Preliminary screening showed that one of the new compounds, namely 7-(4-(2-(3- chlorobenzyloxyimino)-2-(furan-2-yl) ethyl) piperazin-1-yl)-1-cyclopropyl-6- fluoro-4-oxo-1, 4-dihydroquinoline-3-carboxylic acid (6b) showed significant cytotoxic activity against human breast tumor cell lines.