82419-33-8

Usage

Uses

Used in Pharmaceutical Synthesis:
7,8-Difluoro-2,3-dihydro-3-methyl-4H-benzoxazine is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the molecular diversity and properties of the final drug compounds. The presence of fluorine atoms can enhance the pharmacokinetic and pharmacodynamic profiles of the resulting drugs, potentially improving their efficacy and safety.
Used in Organic Chemistry as a Building Block:
In the realm of organic chemistry, 7,8-difluoro-2,3-dihydro-3-methyl-4H-benzoxazine serves as a valuable building block for the creation of complex organic molecules. Its structural features allow for further functionalization and modification, facilitating the development of novel chemical entities with tailored properties for specific applications.
Used in Drug Development:
7,8-Difluoro-2,3-dihydro-3-methyl-4H-benzoxazine is utilized in drug development as a scaffold for the design of new therapeutic agents. Its unique structural elements, including the benzoxazine ring and fluorine substituents, can be exploited to modulate the activity of the compounds, offering opportunities for the discovery of innovative drugs with improved potency, selectivity, and pharmacological profiles.
Used in Material Science:
Beyond its applications in pharmaceuticals and organic chemistry, 7,8-difluoro-2,3-dihydro-3-methyl-4H-benzoxazine may also find use in material science. The properties conferred by the fluorine atoms, such as increased lipophilicity and metabolic stability, could be harnessed in the development of new materials with specialized characteristics for various industrial applications.

InChI:InChI=1/C9H9F2NO/c1-5-4-13-9-7(12-5)3-2-6(10)8(9)11/h2-3,5,12H,4H2,1H3

Upstream product

• 82419-32-7 3,4-difluoro-2-(2-oxopropyloxy)nitrobenzene 
• 112136-69-3 (R)-(+)-7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine 
• 77-92-9 citric acid 
• 117321-74-1 7,8-difluoro-3-methyl-2H-1,4-benzoxazine 
• 82419-26-9 2,3-difluoro-6-nitrophenol 
• 771-69-7 2,3,4-trifluoronitrobenzene 

Downstream Products

• 106939-42-8 (S)-7,8-difluoro-3,4-dihydro-3-methyl-2H-1,4-benzoxazine 
• 112136-69-3 (R)-(+)-7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine 
• 1129-46-0 (R)-(+)-2-phenoxypropionic acid 

Relevant academic research and scientific papers

Palladium Supported on Carbon Nanoglobules as a Promising Catalyst for Selective Hydrogenation of Nitroarenes

The catalysts 1?wt% palladium supported on carbon nanoglobules (CNGs) were shown to be highly active in the liquid-phase hydrogenation of various nitroarenes and provided nearly 100% selectivity to aromatic amines at complete conversion under mild conditions (323?K, 0.5?MPa, 1?h). The catalytic activity (in terms of turnover frequency and substrate conversion) and selectivity depend on the kind of CNGs support, catalyst preparation method and the reaction conditions (solvent nature). The Pd/CNGs catalyst can be repeatedly used while maintaining the same catalytic performance. The excellent performances of Pd/CNGs catalysts can be due to the globular morphology of the supports as well as the absence of micropores and pronounced surface defects. Graphic Abstract: [Figure not available: see fulltext.]

Enantioselective Biocatalytic Reduction of 2 H-1,4-Benzoxazines Using Imine Reductases

A biocatalytic reduction of 2H-1,4-benzoxazines using imine reductases is reported. This process enables a smooth and enantioselective synthesis of the resulting cyclic amines under mild conditions in aqueous media by means of a catalytic amount of the cofactor NADPH as hydride source as well as glucose as the reducing agent used in stoichiometric amounts for in situ cofactor recycling. Several substrates were studied, and the 3,4-dihydro-2H-1,4-benzoxazines were obtained with up to 99% ee. In addition, the efficiency of this reduction process based on imine reductases as catalysts has been demonstrated for one 2H-1,4-benzoxazine on an elevated laboratory scale running at a substrate loading of 10 g L-1 in the presence of a tailor-made whole-cell catalyst.

Synthesizing method of novel ofloxacin intermediate

The invention relates to the field of medicine synthesizing, in particular to a synthesizing method of a novel ofloxacin intermediate as shown in structural formula (II). The synthesizing method includes: allowing 2,3,4-trifluoro nitrobenzene to have reac

Chemoenzymatic Asymmetric Synthesis of 1,4-Benzoxazine Derivatives: Application in the Synthesis of a Levofloxacin Precursor

A versatile and general route has been developed for the asymmetric synthesis of a wide family of 3-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazines bearing different pattern substitutions in the aromatic ring. Whereas hydrolases were not suitable for resoluti

A new convenient method for the synthesis of 2H-1,4-benzoxazine derivatives from nitroketones via intramolecular reductive cyclization

Potentially bioactive 2H-1,4-benzoxazine derivatives could be conveniently prepared in one step from the corresponding nitroketones using 10% palladium on carbon with triethylamine in the presence of hydrogen (Pd/C-TEA-H2) system. Several other

Method of preparing 7,8-difluoro-2,3-dihydro-3-methyl-4H-1, 4-benzoxazine

A method of preparing 7,8-difluoro-2,3-dihydro-3-methyl-4H-1,4 benzoxazine. The method includes the steps of reacting 2,3,4-trifluoroaniline or trifluoronitrobenzene with hydroxyacetone or a derivative thereof under reducing conditions to yield N-(3-hydro

Propoxybenzene derivatives and process for preparing the same

Propoxybenzene derivatives represented by the following formula STR1 wherein Ra represents a nitro group, an amino group which may have a protecting group or an --NHCH=C(COO--C1-6 -Alkyl)2 group, Rb represents a hydrogen atom, a protecting group for the hydroxyl group or a substituted sulfonyl group and Xa and Xb, which may be the same or different, each represents a halogen atom, and processes for preparation thereof are disclosed. These derivatives are useful in preparing antibacterial agents.

Optically active pyridobenzoxazine derivatives and intermediates thereof

An optically action pyridobenzoxazine derivative, a process for preparing the same and a novel intermediate useful for preparing the optically active pyridobenzoxazine derivative are disclosed. The optically active pyridobenzoxazine derivative possesses increased antimicrobial activity and reduced toxicity. The intermediate is useful for preparing such optically active pyridobenzoxazine derivatives such as Ofloxacin and anolog compounds.

Optical resolution of benzoxazines

The invention relates to a process for producing a (±)-3-alkyl-3,4-dihydro-2H-[1,4]benzoxazine derivate of formula (II) by stepwise racemization procedure. STR1 The invention further provides a process for optical resolution through the formation of a salt between a (±)-benzoxazine compound and an optically active form of camphor-10-sulfonic acid. Without requiring the conventional expensive resolution reagents, this process not only assures production of an optically active isomer of compound (II) in high purity but also permits reuse of the optical resolution reagent.

Synthesis and antibacterial activities of substituted 7-oxo-2,3-dihydro-7h-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acids

As part of a search for new synthetic antibacterial agents to combat systemic infection, various analogues of 7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acids were synthesized. Among the compounds newly synthesized, 9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[ 1,2,3-de][1,4]benzoxazine-6-carboxylic acid (DL-8280) showed potent antibacterial activity against Gram-positive and -negative pathogens, including Psedomonas aeruginosa, and its metabolic disposition was shown in separate experimentals to be favorable.