92629-13-5

Usage

Uses

Used in Pharmaceutical Research:
2-PHENYL-1,3-OXAZOLE-5-CARBALDEHYDE is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals due to its versatile chemical structure and potential medicinal properties.
Used in Organic Synthesis:
2-PHENYL-1,3-OXAZOLE-5-CARBALDEHYDE is used as a building block in organic synthesis for the development of new compounds with potential applications in various industries.
Used in Antifungal and Antibacterial Applications:
2-PHENYL-1,3-OXAZOLE-5-CARBALDEHYDE is used as an active ingredient in antifungal and antibacterial formulations, leveraging its potential medicinal properties to combat infections.
Used in Biological Imaging:
2-PHENYL-1,3-OXAZOLE-5-CARBALDEHYDE is used as a fluorescent probe in biological imaging, allowing for the visualization and study of various biological processes.
Used in Enzyme Assays:
2-PHENYL-1,3-OXAZOLE-5-CARBALDEHYDE is used as a marker in various enzyme assays, aiding in the detection and quantification of enzymatic activity.

InChI:InChI=1/C10H7NO2/c12-7-9-6-11-10(13-9)8-4-2-1-3-5-8/h1-7H

Upstream product

• 20662-88-8 2-phenyloxazole 
• 68-12-2 N,N-dimethyl-formamide 
• 238433-75-5 2-phenyl-5-(hydroxymethyl)oxazole 
• 18838-10-3 N-(2-hydroxyethyl)-benzamide 
• 93-89-0 benzoic acid ethyl ester 
• 1464-98-8 N-(prop-2-yn-1-yl)benzamide 
• 591-50-4 iodobenzene 
• 90701-94-3 (E)-5-(iodomethylene)-2-phenyl-4,5-dihydrooxazole 
• 92629-11-3 5-bromo-2-phenyl-1,3-oxazole 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 7127-19-7 2-phenyl-1,3-oxazoline 
• 39819-40-4 ethyl 2-phenyloxazole-5-carboxylate 

Downstream Products

• 106833-79-8 2-phenyl-1,3-oxazole-5-carboxylic acid 
• 263549-83-3 (E)-3-(2-phenyloxazol-5-yl)propenoic acid 
• 39819-42-6 amide of 2-phenyloxazole-5-carboxylic acid 
• 106833-83-4 methyl 2-phenyl-1,3-oxazole-5-carboxylate 
• 106833-92-5 2'-Phenyl-2,5'-bioxazole 
• 106833-86-7 4,5-Dihydro-2'-phenyl-2,5'-bioxazole 
• 106833-87-8 N-(2-Hydroxyethyl)amide of 2-phenyloxazole-5-carboxylic acid 
• 238433-75-5 2-phenyl-5-(hydroxymethyl)oxazole 
• 263549-84-4 diethyl 2-(2-phenyloxazol-5-yl)methylenemalonate 

Relevant academic research and scientific papers

Iodine-mediated aminohalogenation-oxidation to synthesize 2-fluoroalkyl imidazole derivatives

A simple and efficient method of iodine-mediated aminohalogenation-oxidation of fluorinated N’-propargyl amidines to synthesize 2-fluoroalkyl imidazole-5-carbaldehydes was developed. This method showed good functional group compatibility and wide substrat

Catalytic Deprotonative α-Formylation of Heteroarenes by an Amide Base Generated in Situ from Tetramethylammonium Fluoride and Tris(trimethylsilyl)amine

Heteroarene formylations in DMF solution proceed in the presence of an amide base catalyst generated in situ from tetramethylammonium fluoride (TMAF) and tris(trimethylsilyl)amine (N(TMS)3). The reaction proceeds at room temperature and has an operationally simple procedure. Various heteroarenes, including benzothiophene, thiophene, benzothiazole, oxazole, and indole derivatives, can be formylated with high functional group tolerance.

Selenium-π-Acid Catalyzed Oxidative Functionalization of Alkynes: Facile Access to Ynones and Multisubstituted Oxazoles

Unprecedented selenium-catalyzed propargylic oxidation of alkynes is disclosed. Various propargylphosphonates and 3-alkynoates were efficiently converted to valuable ynones via unusual C-C triple bond migration and deselenenylation at a vinyl carbon. By the strategies of tautomerization of enamine intermediate and SN2 displacement, similar conditions were effective for the oxidative difunctionalization of ynamides to afford multisubstituted oxazoles with high regioselectivity. Mechanistic studies revealed these detailed processes.

Preparation of oxazolines and oxazoles via a PhI(OAc)2-promoted cyclization of N-propargylamides

A metal-free cyclization of N-propargylamides for the synthesis of various oxazolines and oxazoles via a 5-exo-dig process is presented. Using (diacetoxyiodo)benzene (PIDA) as a reaction promoter and lithium iodide (LiI) as an iodine source, intramolecula

Versatile Photochemical Reactivity of Diverse Substituted 2-, 4- and 5-(o-Vinylstyryl)oxazoles

To study the effects of the position of the hexatrienyl moiety on the oxazole ring, novel substituted cis/trans-2/4/5-(2-vinylstyryl)oxazoles have been synthesized. These novel compounds were prepared by Wittig reaction from the diphosphonium salt of α,α′-o-xylenedibromide, formaldehyde and the corresponding 2-methyl-4-, 4-methyl-2-, 2-pheny-5- and 4-methyl-5-oxazolecarbaldehyde, respectively. Aldehydes were synthesized by using several synthetic approaches. By applying intramolecular photocycloaddition, 2-methyl-4-(2-vinylstyryl)oxazole afforded, as major product, fused oxazoline-benzobicyclo[3.2.1]octene with small quantities of 4-(1,2-dihydronaphthalen-2-yl)-2-methyloxazole, as electrocyclization product. Upon irradiation of 4-methyl-5-(2-vinylstyryl)oxazole, endo- and exo-benzobicyclo[2.1.1]hexene products were formed by [2+2] cycloaddition; this was the first instance of the 1,4-closure to the bicyclo[2.1.1]hexene skeleton in the 2-, 4-, and 5-oxazole-stilbene derivatives studied so far. Derivatives 2-phenyl-5- and 4-methyl-2-(2-vinylstyryl)oxazole did not react and gave only high-weight molecular products but were crucial as a comparison in the overall mechanistic study. We have found that, depending on the position of the hexatrienyl moiety in the oxazole ring, as well as on the position of the methyl/phenyl substituents, these new vinylstyryl-2/4/5-oxazole derivatives show diverse photochemical behavior.

Iodine/Visible Light Photocatalysis for Activation of Alkynes for Electrophilic Cyclization Reactions

Photocatalytic organic synthesis needs photocatalysts to initiate the reactions and to control the reaction paths. Available photocatalytic systems rely on electron transfer or energy transfer between the photoexcited catalysts and the substrates. We expl

Merging gold catalysis, organocatalytic oxidation, and Lewis acid catalysis for chemodivergent synthesis of functionalized oxazoles from: N -propargylamides

Novel catalytic systems consisting of cationic gold complexes, N-hydroxyphthalimide (NHPI), and transition-metal-based Lewis acids have been developed for the one-pot synthesis of functionalized oxazoles from N-propargylamides with excellent functional group tolerance. These transformations demonstrated the excellent compatibility of homogeneous gold catalysis with organocatalytic oxidative carbon-nitrogen bond formations using tert-butyl nitrite as the terminal oxidant. Moreover, oxazolecarbonitriles or carboxamides can be easily synthesized in a one-pot protocol according to the different synthetic requirements.

2,4-Imidazolinedione heterocyclic derivative, and preparation method and use thereof

The invention belongs to the field of chemical medicines, and concretely relates to a 2,4-imidazolinedione heterocyclic derivative, and a preparation method and a use thereof. The structure of the 2,4-imidazolinedione heterocyclic derivative is represented by formula I. The invention also provides the preparation method and the use of the 2,4-imidazolinedione heterocyclic derivative. The 2,4-imidazolinedione heterocyclic derivative has a good inhibition effect on Pim-1 protein kinase micro-molecules, and has important exploitation application prospect.

Single-Step Synthesis of Iodinated Oxazoles from N-Propargyl Amides Mediated by I2/Iodosylbenzene/Trimethylsilyl Trifluoromethanesulfonate Systems

A combination of I2, iodosylbenzene, and trimethylsilyl trifluoromethanesulfonate (TMSOTf) is effective for single-step synthesis of iodinated oxazoles from N-propargyl amides via the aromatization of the iodocyclized intermediates, which has difficulty proceeding through conventional iodocyclization methods. Compared to the former method consisting of the metal-catalyzed cyclization of N-propargyl amides followed by halogenation of alkylideneoxazolines, the present reaction provides a facile and metal-free procedure.

Catalysis and synthesis method of heterocyclic nitrile compound

The invention discloses a catalysis and synthesis method of a heterocyclic nitrile compound. The method includes the following steps that firstly, a propargylamide compound, tert-butyl nitrite, hydroxyl phthalic diamide, a catalyst and an auxiliary catalyst are added into a pressure-resistant sealed reaction container containing a solvent, nitrogen is introduced, and then stirring reaction is conducted in oil bath at 50-100 DEG C; secondly, after reaction, the reaction product of the first step is taken out from the pressure-resistant sealed reaction container and cooled to room temperature, ethyl acetate is added and fully mixed, and an organic phase is obtained; thirdly, the solvent in the organic phase obtained in the second step is spin-dried, purification is conducted through a silica column, and then the product is washed with eluent which is a mixed solution of petroleum ether and ethyl acetate. In the catalysis and synthesis method, under the participation of transition metal, the propargylamide compound reacts through bimetallic catalysis reaction to obtain the heterocyclic nitrile compound, the reaction can quickly build the heterocyclic nitrile compound, cyano groups can be converted into various groups, and nitrile compounds can be selectively obtained.