13213-88-2

Usage

Uses

Used in Agricultural Applications:
1,4-dihydro-2H-3,1-benzoxazin-2-one is used as a natural defense compound in plants for protecting them from pathogens and herbivores. Its presence in the Poaceae family, including wheat, maize, and rye, contributes to the plants' resistance against various threats.
Used in Pharmaceutical Applications:
1,4-dihydro-2H-3,1-benzoxazin-2-one is used as a potential therapeutic agent for its anti-inflammatory and anti-cancer activities. Its unique chemical structure and biological properties make it a promising candidate for further research and development in the field of medicine.
Used in Research Applications:
1,4-dihydro-2H-3,1-benzoxazin-2-one is used as a subject of study in scientific research to explore its pharmacological properties and potential applications in agriculture and medicine. Its unique structure and biological activities provide valuable insights for the development of new compounds and therapies.

InChI:InChI=1/C8H7NO2/c10-8-9-7-4-2-1-3-6(7)5-11-8/h1-4H,5H2,(H,9,10)

Upstream product

• 5344-90-1 2-Aminobenzyl alcohol 
• 75-44-5 phosgene 
• 201230-82-2 carbon monoxide 
• 118-48-9 isatoic anhydride 
• 33832-98-3 2-hydroxymethylbenzamide 
• 42250-17-9 ethyl N-[2-(hydroxymethyl)phenyl]carbamate 
• 17374-20-8 1,4-dihydro-benzo[d][1,3]oxazine-2-thione 
• 7722-84-1 dihydrogen peroxide 
• 139503-14-3 6-iodo-1-methyl-2-oxo-1,2-dihydro-4H-3,1-benzoxazine 
• 503-38-8 trichloromethyl chloroformate 
• 82091-12-1 dimethyl 2,2’-(carbonylbis(oxy))dibenzoate 
• 20615-76-3 2-azidobenzyl alcohol 
• 57-13-6 urea 
• 3582-05-6 trifluoromethyl trifluoromethanesulfonate 

Downstream Products

• 5344-90-1 2-Aminobenzyl alcohol 
• 35382-70-8 2-(2-oxo-4H-benzo[d][1,3]oxazin-1-yl)-acetamide 
• 13213-91-7 1-(4-chloro-benzoyl)-1,4-dihydro-benzo[d][1,3]oxazin-2-one 
• 13213-94-0 6-chloro-1-methyl-4-phenyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one 
• 1017783-09-3 6-bromo-1,4-dihydro-2H-3,1-benzoxazin-2-one 
• 1418201-57-6 1-(2-fluoro-4-(1-methyl-1H-pyrazol-4-yl)benzyl)-1H-benzo[d][1,3]oxazin-2(4H)-one 
• 1383579-68-7 C₁₅H₁₂ClFN₂O₄S 
• 130020-41-6 [4-(Cyclohexyl-methyl-amino)-1-ethyl-1,2,3,4-tetrahydro-quinolin-8-yl]-methanol 
• 130020-38-1 (4-Cyclohexylamino-1-ethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-methanol 
• 112646-14-7 1H,3H,5H,6H,7H-3,7-Dioxopyrido<3,2,1-ij><3,1>benzoxazine 

Relevant academic research and scientific papers

Selenium-catalyzed reductive carbonylation of 2-nitrophenols to 2-benzoxazolones

2-Benzoxazolones or 2-benzimidazolones are synthesized in moderate to good yields in the presence of a base (KOH, NaOH, KOAc, NEt3, DBU) at atmospheric pressure or under a high pressure of CO by one-pot reductive carbonylation of 2-nitrophenols or 2-nitroaniline in the presence of selenium as catalyst. Besides the effect of base, the effects of solvent and temperature on the reaction were investigated at high or atmospheric pressure. Contrasting results were obtained for 2-benzoxazolones or 2-benzimidazolone at high and atmospheric pressures. Moreover, phase-transfer catalysis was exhibited. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Selenium-catalyzed oxidative carbonylation of 2-aminobenzyl alcohol to give 1,4-dihydro-2 H -3,1-benzoxazin-2-one

An efficient, economical, and phosgene-free approach was developed for the preparation of 1,4-dihydro-2H-3,1-benzoxazin-2-one from 2-aminobenzyl alcohol. In terms of its key features, this reaction uses the cheap and recyclable non-metal selenium as a catalyst instead of the noble metal palladium; carbon monoxide as a carbonylation agent instead of virulent phosgene or one of its derivatives; and oxygen as an oxidant. The selenium-catalyzed oxidative carbonylation reaction of 2-aminobenzyl alcohol proceeded efficiently in a single pot in the presence of triethylamine to afford 1,4-dihydro-2H-3,1-benzoxazin-2-one in 87% yield. Furthermore, the selenium catalyst was readily recovered and recycled, affording a product yield of 80% after five cycles.

Synthesis of 1,4-dihydro-benzo[d][1,3]oxazin-2-ones from phthalides via an aminolysis-Hofmann rearrangement protocol

A simple two-step procedure for the conversion of readily available phthalides to the corresponding benzoxazinones was developed. Initial ring-opening aminolysis to form a primary 2-hydroxymethylbenzamide, followed by reaction with bis(trifluoroacetoxy)iodobenzene (BTI) conveniently, provided a variety of 4-substituted benzoxazinones.

Synthesis of benzo-fused five- and six-membered heterocycles by palladium-catalyzed cyclocarbonylation

A novel and simple synthetic methodology, based on palladium-catalyzed cyclocarbonylation reaction, is presented for preparing five- and six-membered benzo-fused heterocycles. A mechanism for the process is also proposed and discussed.

Synthesis of fullerotetrahydroquinolines by cycloaddition reaction of C60 with aza-ortho-xylylenes

This paper reports on the successful synthesis of fullerotetrahydroquinolines by using in sire generated aza-ortho-xylylenes using a Diels-Alder reaction.

Metal catalyzed deoxygenation by carbon monoxide of o-substituted nitrobenzenes. Synthesis of 1,4-dihydro-2H-3,1-benzoxazin-2-one derivatives

The reductive carbonylation of o-nitrobenzylalcohols, o-NO2C6H4CR1R2OH 1 = R2 = H (1); R1 = R2 = CH3 (2); R1 = H, R2 = CH3 (3); R1 = H, R2 = C6H5 (4)>, catalyzed by ruthenium and palladium-based catalytic systems gives the corresponding 1,4-dihydro-2H-3,1-benzoxazin-2-one derivatives, 1a-4a.Reaction conditions used were 20-60 atm of carbon monoxide and 100-170 deg C.The palladium catalyst has been shown to be far superior to the ruthenium catalyst in this reaction as far as selectivity is concerned.By carbonylation of o-nitrophenethylalcohol (5) with the palladium system as catalyst a mixture of the monomeric 5a and dimeric 5b cyclic carbamates has been obtained.

A new synthetic method of 1,4-dihydro-2h-3,1-benzoxazin-2-ones: Selenium-catalyzed reductive carbonylation of aromatic nitro compounds with carbon monoxide

It was confirmed that selenium catalyzed the reaction of 2-nitrobenzyl alcohols with carbon monoxide to afford 1,4-dihydro-2H-3,1-benzoxazin-2-ones in good yields. Similarly, seven-membered cyclic carbamate was prepared by the reaction of 2-(2-nitrophenyl)ethanol with carbon monoxide.

Electrochemical access to benzimidazolone and quinazolinone derivatives: Via in situ generation of isocyanates

Isocyanates are the key intermediates for several organic transformations towards the synthesis of diverse pharmaceutical targets. Herein, we report the development of an oxidant-free protocol for electrochemical in situ generation of isocyanates. This strategy highlights expedient access to benzimidazolones and quinazolinones and eliminates the need for exogenous oxidants. Furthermore, detailed mechanistic studies provide strong support towards our hypothesis of in situ isocyanate generation. This journal is

INHIBITORS OF PHOSPHOLIPID SYNTHESIS AND METHODS OF USE

Inhibitors of Glycerol 3-Phosphate Acyltransferase (GPAT) are provided; and methods of use in the treatment of cancer; and treatment of conditions relating to metabolic syndrome, hyperlipidemia, infection and inflammation.

Versatile Cp*Co(III)(LX) Catalyst System for Selective Intramolecular C-H Amidation Reactions

Herein, we report the development of a tailored cobalt catalyst system of Cp*Co(III)(LX) toward intramolecular C-H nitrene insertion of azidoformates to afford cyclic carbamates. The cobalt complexes were easy to prepare and bench-stable, thus offering a convenient reaction protocol. The catalytic reactivity was significantly improved by the electronic tuning of the bidentate LX ligands, and the observed regioselectivity was rationalized by the conformational analysis and DFT calculations of the transition states. The superior performance of the newly developed cobalt catalyst system could be broadly applied to both C(sp2)-H and C(sp3)-H carbamation reactions under mild conditions.