39522-26-4

Usage

Uses

Used in Pharmaceutical Industry:
6-METHYL-2H-1,4-BENZOXAZIN-3(4H)-ONE is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of organic chemistry, 6-METHYL-2H-1,4-BENZOXAZIN-3(4H)-ONE is used as a versatile building block for the creation of a wide range of organic molecules. Its reactivity and structural diversity make it a valuable asset in the synthesis of complex organic compounds.
Used in Agrochemical Industry:
6-METHYL-2H-1,4-BENZOXAZIN-3(4H)-ONE is utilized as a starting material in the development of agrochemicals, such as pesticides and herbicides. Its structural properties enable the creation of compounds with targeted biological activities, contributing to the advancement of crop protection strategies.
Used in Dye and Pigment Industry:
6-METHYL-2H-1,4-BENZOXAZIN-3(4H)-ONE is also employed in the production of dyes and pigments due to its ability to form colored compounds. Its incorporation into the chemical structure of dyes and pigments can result in a wide range of colors and shades, expanding the palette of options available in the industry.
Used in Research and Development:
6-METHYL-2H-1,4-BENZOXAZIN-3(4H)-ONE is a valuable compound in the field of research and development, particularly in the study of organic chemistry and the development of new materials. Its unique structure and reactivity make it an interesting subject for scientific investigation and potential applications in various fields.

InChI:InChI=1/C9H9NO2/c1-6-2-3-8-7(4-6)10-9(11)5-12-8/h2-4H,5H2,1H3,(H,10,11)

Upstream product

• 134997-67-4 2-<(2-chloroacetyl)amino>-4-methylphenol 
• 79-04-9 chloroacetyl chloride 
• 120-71-8 Cresidine 
• 95-84-1 3-amino-4-hydroxytoluene 
• 119-33-5 4-methyl-2-nitrophenol 
• 431994-40-0 (4-methyl-2-nitro-phenoxy)-acetic acid ethyl ester 
• 105-36-2 ethyl bromoacetate 
• 1247390-41-5 2-(4-methyl-2-nitrophenoxy)acetonitrile 
• 615-74-7 2-chloro-5-methylphenol 
• 79-07-2 Chloroacetamide 
• 38768-63-7 methyl p-tolyloxyacetate 
• 106-44-5 p-cresol 
• 598-42-5 glycolamide 
• 95-75-0 3,4-Dichlorotoluene 

Downstream Products

• 62490-79-3 2-benzylidene-6-methyl-4H-benzo[1,4]oxazin-3-one 
• 6238-85-3 [4-Methyl-2-(3-trifluoromethyl-benzoylamino)-phenoxy]-acetic acid 
• 6529-99-3 4-Methyl-2-benzamido-phenoxyessigsaeure 
• 6239-19-6 [2-(4-Chloro-benzoylamino)-4-methyl-phenoxy]-acetic acid 
• 6548-54-5 [2-(3,4-Dichloro-benzoylamino)-4-methyl-phenoxy]-acetic acid 
• 96753-80-9 8-Methyl-2,4-dihydro-5-oxa-2,3,9b-triaza-cyclopenta[a]naphthalen-1-one 
• 96780-80-2 C₁₆H₁₆N₄OS 
• 62490-70-4 2-benzylidene-4-(3-dimethylamino-propyl)-6-methyl-4H-benzo[1,4]oxazin-3-one 
• 71472-57-6 6-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine 
• 1245276-82-7 (Z)-2,6-dibromo-4-{(6-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-ylidene)methyl}phenyl acetate 
• 1245277-07-9 (Z)-6-methyl-2-(3,4,5-trimethoxybenzylidene)-2H-benzo[b][1,4]oxazin-3-(4H)-one 
• 1307844-93-4 C₂₁H₂₁ClN₄O₂S 
• 104971-88-2 2-(4-Methoxy-phenyl)-8-methyl-4H-5-oxa-3,9b-diaza-cyclopenta[a]naphthalene 
• 104971-87-1 2-(4-Chloro-phenyl)-8-methyl-4H-5-oxa-3,9b-diaza-cyclopenta[a]naphthalene 

Relevant academic research and scientific papers

Intramolecular cyclization of N-hydroxy-2-phenoxyacetamides and 3-phenoxypropanamides

Abstract: A novel route for the preparation of 2H-1,4- benzoxazin-3(4H)one and 1,5 benzoxazepinones by intramolecular cyclization of N-hydroxy 2-phenoxyacetamide and N-hydroxy -3 phenoxypropanamide using PPA and Lewis acid has been discussed. Graphical abstract: [Figure not available: see fulltext. Caption: Preparation of 2H-1,4- benzoxazin-3(4H)one and 1,5 benzoxazepinones by electrophilic aromatic substitution from N-hydroxy 2-phenoxyacetamide and N-hydroxy -3 phenoxypropanamide and their acetyl and benzoyl derivatives using PPA and Lewis acids.]

Synthesis technology of 1,4-benzoxazinone compound

The invention relates to a synthesis technology of benzoxazinone compounds represented by formula I. The technology is characterized in that a dichlorobenzene derivative represented by formula II reacts with ethanolamide represented by formula III in the presence of a catalyst and an inorganic alkali to obtain the compound of formula I. R in the formula I and the formula II is selected from hydrogen, an amino group, a nitro group, a C1-6 alkyl group, a C1-6 alkoxy group and a hydroxyl group. The technology is a one-pot reaction method, realizes one-step direct cyclization, and has the advantages of simple reaction conditions, convenience in treatment, safe and highly-effective process, and high yield.

Using gene expression database to uncover biology functions of 1,4-disubstituted 1,2,3-triazole analogues synthesized via a copper (I)-catalyzed reaction

We have synthesized bioactive 1,4-disubstituted 1,2,3-triazole analogues containing 2H-1,4-benzoxazin-3-(4H)-one derivatives via 1,3-dipolar cycloaddition in the presence of CuI. All the reactions proceeded smoothly and afforded its desired products in excellent yields. Among these analogues, 3y exhibited a better cytotoxic effect on human hepatocellular carcinoma (HCC) Hep 3B cells and displayed less cytotoxicity on normal human umbilical vein endothelial cells, compared with Sorafenib, a targeted therapy for advanced HCC. 3y also induced stronger apoptosis and autophagy. Addition of curcumin enhanced 3y-induced cytotoxicity by further induction of autophagy. Using gene expression signatures of 3y to query Connectivity Map, a glycogen synthase kinase-3 inhibitor (AR-A014418) was predicted to display similar molecular action of 3y. Experiments further demonstrate that AR-A014418 acted like 3y, and vice versa. Overall, our data suggest the chemotherapeutic potential of 3y on HCC.

Synthetic technology for preparing 1,4-benzoxazinone through microwave process

The invention relates to a preparation method for a benzoxazine compound. The method comprises the following steps: adding the compound shown as formula II, methyl alcohol and catalyst into a reactor; reacting under the existence of catalyst and alkali; and performing post-processing after ending the reaction, thereby acquiring the compound shown as formula I. In the formula, R group is selected from hydrogen, amino, nitro, C1-C6 alkyl, C1-C6 alkoxy and hydroxy; alkyl is selected from methyl, ethyl and isopropyl; alkoxy is selected from methoxy group, ethyoxyl and isopropoxy. The method is low in cost of raw materials, is safe and reliable, is completed under normal temperature and normal pressure and is simple in process.

Efficient synthesis of benzene-fused 6/7-membered amides: Via Xphos Pd G2 catalyzed intramolecular C-N bond formation

An efficient approach for benzene-fused 6/7-membered amides via intramolecular amidation of aryl chlorides catalyzed by a Buchwald-Hartwig second generation Pd catalyst (Xphos Pd G2) has been successfully developed. This catalyst system allows the primary amides which have only modest nucleophilicity to be coupled successfully even with electron rich aryl chlorides in short reaction time. The intramolecular amidation reaction also has good chemoselectivity and excellent functional group compatibility.

New Approach to 1,4-Benzoxazin-3-ones by Electrochemical C?H Amination

1,4-Benzoxazin-3-ones are important structural motifs in natural products and bioactive compounds. Usually, the synthesis of benzoxazinones requires transition-metal catalysts and pre-functionalized substrates such as aryl halides. However, the anodic C?H

Microwave-assisted synthesis of benzo-[1,4]-oxazinones using MeO-PEG-OMe as solvent

Efficient one-pot microwave-assisted synthesis of various benzo-[1,4]-oxazinones via Smiles rearrangement is described. Treatment of 2-chloroacetamide, substituted 2-chlorophenols and cesium carbonate in MeO-PEG-OMe (2,000) as solvent afforded the corresp

A simple and facile route for the synthesis of 2H-1,4-benzoxazin-3-(4H)- ones via reductive cyclization of 2-(2-nitrophenoxy)acetonitrile adducts in the presence of Fe/acetic acid

A simple route for the synthesis of 1,4-benzoxazin-3-(4H)-ones is described herein. This method involves the reductive cyclization of 2-(2-nitrophenoxy) acetonitrile adducts in the presence of Fe/acetic acid in good to excellent yields. This system was compatible with various other functional groups.

[Omim][BF4], a green and recyclable ionic liquid medium for the one-pot chemoselective synthesis of benzoxazinones

An efficient procedure for the one-pot chemoselective synthesis of 2H-benzo[b][1,4]oxazin-3(4H)-one derivatives from their corresponding o-aminophenols is developed using DBU in the ionic liquid [omim][BF4]. Upon completion of the reaction and separation of the product, the ionic liquid is recovered and successfully reused over nine recycles without any noticeable loss of performance.

An efficient cascade synthesis of various 2H-1,4-benzoxazin-3-(4H)-ones from o-halophenols and 2-halo-amides catalyzed by CuI

A novel and efficient one-pot cascade synthesis of 2H-1,4-benzoxazin-3-(4H) -ones has been developed through copper-catalyzed coupling of o-halophenols and 2-halo-amides. Various 2H-1,4-benzoxazin-3-(4H)-ones with diversity at three substituents on their