19226-36-9

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
3-phenyl-5H-1,4,2-dioxazol-5-one is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure allows for the development of new drugs with improved efficacy and safety profiles.
Used in Organic Chemistry:
As a building block, 3-phenyl-5H-1,4,2-dioxazol-5-one is utilized in organic chemistry for the creation of diverse organic compounds, contributing to advancements in chemical research and the discovery of novel materials.
Used in Antimicrobial and Antiviral Applications:
Phthalazone is used as an antimicrobial and antiviral agent due to its demonstrated biological activities. Its potential in this area is currently under investigation, with the aim of developing new treatments for infectious diseases.
Used in Dyes and Pigments Industry:
3-phenyl-5H-1,4,2-dioxazol-5-one is used as a component in the preparation of dyes and pigments. Its ability to form colored complexes with metal ions makes it a valuable asset in the development of new colorants for various applications.
Overall, 3-phenyl-5H-1,4,2-dioxazol-5-one is a multifaceted compound with significant potential across several industries, particularly in the development of new drugs, materials, and colorants.

Upstream product

• 75-44-5 phosgene 
• 495-18-1 Benzohydroxamic acid 
• 94267-72-8 N-dimethylcarbamoyloxy-benzamidine 
• 89323-62-6 S-ethoxycarbonylmethyl chlorothioformate 
• 541-41-3 chloroformic acid ethyl ester 
• 2941-64-2 Ethyl chlorothioformate 
• 1885-14-9 phenyl chloroformate 
• 530-62-1 1,1'-carbonyldiimidazole 
• 98-88-4 benzoyl chloride 
• 93-58-3 benzoic acid methyl ester 
• 10364-94-0 1-benzoylimidazole 
• 65-85-0 benzoic acid 
• 102-09-0 bis(phenyl) carbonate 

Downstream Products

• 38584-22-4 5-methoxy-4,4-dimethyl-2-phenyl-4,5-dihydro-oxazole 
• 103-71-9 phenyl isocyanate 
• 1198745-93-5 C₁₂H₁₄N₂O₄ 
• 855410-81-0 5-(benzo[d][1,3]dioxol-5-yl)-2-phenyl-4,5-dihydrooxazole 
• 92-71-7 2,5-diphenyloxazole 
• 1373758-48-5 5-(4-ethoxyphenyl)-2-phenyloxazole 
• 62921-42-0 5-(4-methoxyphenyl)-2-phenyl-1,3-oxazole 
• 54090-90-3 N-(methyl(oxo)(phenyl)-λ⁶-sulfanylidene)benzamide 
• 102-07-8 bis(diphenyl)urea 
• 42397-44-4 N-benzoyl methyl phenyl sulfimide 
• 1627203-99-9 N-benzoyl cyclohexylmethylsulfimide 
• 1627203-95-5 N-benzoyl cyclohexylmethylsulfoximine 
• 31280-33-8 N-(benzoyl)-S,S-dimethylsulfoximine 
• 19397-91-2 N-(dimethyl-λ⁴-sulfanylidene)benzamide 

Relevant academic research and scientific papers

Crossover inhibition as an indicator of convergent evolution of enzyme mechanisms: A β-lactamase and a N-terminal nucleophile hydrolase

O-Aryloxycarbonyl hydroxamates and 1,3,4-oxathiazol-2-ones have been identified as covalent inhibitors of β-lactamases and proteasomes, respectively. The products of these inhibition reactions are remarkably similar, involving carbonyl cross-linking of the active sites. We have cross-checked these inhibitors, showing that the former inhibit proteasomes and the latter β-lactamases, to form the same inactive carbonyl adducts. These results are discussed in terms of similarities of the active site structures and catalytic mechanisms. It is likely that a mechanistic imperative has led to convergent evolution of these enzyme active sites, of a β-lactam-recognizing enzyme and a N-terminal protease belonging to different amidohydrolase superfamilies.

Rhodium(III)-Catalyzed Aldehyde C?H Activation and Functionalization with Dioxazolones: An Entry to Imide Synthesis

A rhodium(III)-based catalytic system has been used to develop a C?H bond activation of benzaldehyde derivatives and subsequent functionalization with dioxazolones in order to afford imides. The importance of the nature of the directing group to perform selectively the aldehydic C?H bond activation has been highlighted. The scope investigation showed that this transformation could be applied to various dioxazolones and many benzaldehyde derivatives as well as an acrolein derivative. Derivatization reactions of the imide products demonstrated the synthetic utility of this rhodium-catalyzed aldehydic C?H amidation.

Cu(II)-Catalyzed C-H Amidation/Cyclization of Azomethine Imines with Dioxazolones via Acyl Nitrenes: A Direct Access to Diverse 1,2,4-Triazole Derivatives

We report a Cu(II)-catalyzed C-H amidation/cyclization of azomethine imines with dioxazolones as acyl nitrene transfer reagents under additive-and ligand-free conditions. An array of 1,2,4-triazolo[1,5-a]pyridine derivatives were afforded in moderate to good yields with excellent functional group tolerance. In addition, scale-up reaction and photoluminescence properties were discussed.

Direct synthesis of benzoxazinones via Cp*Co(III)-catalyzed C–H activation and annulation of sulfoxonium ylides with dioxazolones

A highly novel and direct synthesis of benzoxazinones was developed via Cp*Co(III)-catalyzed C–H activation and [3 + 3] annulation between sulfoxonium ylides and dioxazolones. The reaction is conducted under base-free conditions and tolerates various functional groups. Starting from diverse readily available sulfoxonium ylides and dioxazolones, a variety of benzoxazinones could be synthesized in one step in 32%-75% yields.

Silver-Catalyzed Acyl Nitrene Transfer Reactions Involving Dioxazolones: Direct Assembly of N-Acylureas

Dioxazolones and isocyanides are useful synthetic building blocks, and have attracted significant attention from researchers. However, the silver-catalyzed nitrene transfer reaction of dioxazolones has not been investigated to date. Herein, a silver-catalyzed acyl nitrene transfer reaction involving dioxazolones, isocyanides, and water was realized in the presence of Ag2O to afford a series of N-acylureas in moderate to good yields.

Chemical Upcycling of Waste Poly(bisphenol A carbonate) to 1,4,2-Dioxazol-5-ones and One-Pot C?H Amidation

Chemical upcycling of poly(bisphenol A carbonate) (PC) was achieved in this study with hydroxamic acid nucleophiles, giving rise to synthetically valuable 1,4,2-dioxazol-5-ones and bisphenol A. Using 1,5,7-triazabicyclo[4.4.0]-dec-5-ene (TBD), non-green carbodiimidazole or phosgene carbonylation agents used in conventional dioxazolone synthesis were successfully replaced with PC, and environmentally harmful bisphenol A was simultaneously recovered. Assorted hydroxamic acids exhibited good-to-excellent efficiencies and green chemical features, promising broad synthetic application scope. In addition, a green aryl amide synthesis process was developed, involving one-pot depolymerization from polycarbonate to dioxazolone followed by rhodium-catalyzed C?H amidation, including gram-scale examples with used compact discs.

Thioether-Directed NiH-Catalyzed Remote γ-C(sp3)-H Hydroamidation of Alkenes by 1,4,2-Dioxazol-5-ones

A NiH-catalyzed thioether-directed cyclometalation strategy is developed to enable remote methylene C-H bond amidation of unactivated alkenes. Due to the preference for five-membered nickelacycle formation, the chain-walking isomerization initiated by the NiH insertion to an alkene can be terminated at the γ-methylene site remote from the alkene moiety. By employing 2,9-dibutyl-1,10-phenanthroline as the ligand and dioxazolones as the reagent, the amidation occurs at the γ-C(sp3)-H bonds to afford the amide products in up to 90% yield (>40 examples) with remarkable regioselectivity (up to 24:1 rr).

1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: An Efficient Synthesis of 2-Quinolinones via β-Keto Amides

Under thermal conditions, 1,4,2-dioxazol-5-ones are known to undergo decarboxylation followed by Lossen's rearrangement to yield isocyanates. Described herein is the in situ trapping of the resulting isocyanates with carbon nucleophiles to synthesize β-keto amides. Furthermore, a general and mild method for the conversion of the resulting β-keto amides into quinolin-2-ones is reported.

Interweaving Visible-Light and Iron Catalysis for Nitrene Formation and Transformation with Dioxazolones

Herein, visible-light-driven iron-catalyzed nitrene transfer reactions with dioxazolones for intermolecular C(sp3)-N, N=S, and N=P bond formation are described. These reactions occur with exogenous-ligand-free process and feature satisfactory to excellent yields (up to 99 %), an ample substrate scope (109 examples) under mild reaction conditions. In contrast to intramolecular C?H amidations strategies, an intermolecular regioselective C?H amidation via visible-light-induced nitrene transfer reactions is devised. Mechanistic studies indicate that the reaction proceeds via a radical pathway. Computational studies show that the decarboxylation of dioxazolone depends on the conversion of ground sextet state dioxazolone-bounding iron species to quartet spin state via visible-light irradiation.

Co(III)-Catalyzed C-H Amidation of Nitrogen-Containing Heterocycles with Dioxazolones under Mild Conditions

A cobalt(III)-catalyzed C-8 selective C-H amidation of quinoline N-oxide using dioxazolone as an amidating reagent under mild conditions is disclosed. The reaction proceeds efficiently with excellent functional group compatibility. The utility of the current method is demonstrated by gram scale synthesis of C-8 amide quinoline N-oxide and by converting this amidated product into functionalized quinolines. Furthermore, the developed catalytic method is also applicable for C-7 amidation of N-pyrimidylindolines and ortho-amidation of benzamides.