133229-67-1

Upstream product

• 133229-58-0 α,4-diphenyl-2-oxazolemethanol 
• 98-86-2 acetophenone 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 100-42-5 styrene 
• 16717-64-9 1-azidostyrene 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 7654-06-0 3-phenyl-2H-azirine 

Relevant academic research and scientific papers

Dimethyl Sulfoxide Oxygen Donor-Based Annulation of Ketones and Ammonium Persulfate: Regioselective Synthesis of 2,4-disubstituted Oxazoles

An efficient protocol for the synthesis of substituted oxazoles via an annulation of ketones, DMSO, and ammonium is reported. DMSO is first found to serve as oxygen donor in annulation resulting in regioselective synthesis of 2,4-disubstituted oxazoles. With the optimized conditions in hand, 22 examples of 2,4-disubstituted oxazoles are obtained from readily available substrates. The protocol can be also applied in cross-condensation reactions between methyl ketones and non-methyl ketones resulting 4 examples of 2,4,5-trisubstituted oxazoles. Moreover, we have successfully applied the protocol into gram-scale representing good yields, that showing the potential practicality in organic synthesis. Based on control experiments and literature, a plausible reaction mechanism was proposed in our work. (Figure presented.).

Synthesizing method of 2,4-disubstituted oxazole

The invention discloses a synthesizing method of 2,4-disubstituted oxazole. The method includes: allowing a methyl ketone compound to have cyclization reaction in a DMSO solution system containing ammonium persulfate and haloid and/halogen simple substance to obtain the 2,4-disubstituted oxazole. The method has the advantages that the cheap methyl ketone compound, quaternary ammonium salt, dimethyl sulfoxide and the like are used as the raw materials to synthesize the 2,4-disubstituted oxazole compound in a high yield manner through a one-pot method under mild reaction conditions and without the catalytic effects of heavy metal or precious metal, and industrial production is benefited.

Method for constructing 2,4-diaryloxazole by acetophenone compound, ammonium persulfate and dimethylsulfoxide jointly

The invention discloses a method for constructing 2,4-diaryloxazole by acetophenone compound, ammonium persulfate and dimethylsulfoxide jointly. The method includes that the acetophenone compound is subjected to cyclization reaction in DMSO (dimethylsulfoxide) solution which contains ammonium persulfate and TBAI (tetrabutylammonium iodide) to obtain 2,4-diaryloxazole. According to the method, thecheap acetophenone compound, ammonium persulfate, dimethylsulfoxide and the like are used as raw materials for one-pot high-yield synthesis of 2,4-diaryloxazole compounds under mild reaction conditions without heavy metal or precious metal catalytic action, and industrial production is benefited.

Synthesis method of 2,4 diaryl oxazole

The invention discloses a synthesis method of 2,4 diaryl oxazole. According to the synthesis method, a cyclization reaction is performed on an aryl ketone compound in a DMSO solution system containingammonium persulfate and halogenated quaternary ammonium salt to obtain the 2,4 diaryl oxazole. By the method, the aryl ketone compound, the quaternary ammonium salt, dimethyl sulfoxide and the like which are cheap are used as raw materials, and under a mild reaction condition and no catalysis of heavy metal or precious metal, high-yield synthesis of the 2,4 diaryl oxazole compound is achieved bya one-pot method; the method is beneficial for industrial production.

Visible-Light Photoredox Catalyzed Three-Component Cyclization of 2H-Azirines, Alkynyl Bromides, and Molecular Oxygen to Oxazole Skeleton

A novel three-component cyclization of 2H-azirines, alkynyl bromides, and molecular oxygen under visible-light photoredox catalysis at room temperature has been developed, which provides a direct approach to a wide range of substituted oxazoles in moderate to good yields.

Substituted Oxazoles: Synthesis via Lithio Intermediates

Reactions of 2-α-, 2-, 4-, and 5-lithiooxazoles are used to prepare various substituted derivatives.Previously unrecognized time dependence for the reaction of a 2-lithiooxazole with benzaldhyde is described, and a rationale for this behavior is offered.Competitive reactions occur when the readily available 2,5-diphenyloxazole is treated with n-butyllithium.Deprotonation of the ortho position of the 2-phenyl group and addition of n-butyl to the 2-position of the oxazole compete with the desired 4-lithiation.The use of sec-butyllithium/catalytic lithium tetramethylpiperidide allows preferential formation of 4-lithio-2,5-diphenyloxazole.This intermediate has been converted to the 4-bromo, -methyl, -hydroxybenzyl, -benzoyl, and -trialkylsilyl derivatives.Lithiation of 2,4-diphenyloxazole and subsequent trimethylsilylation occur readily at the 5-position.Deprotonation of 2-alkyloxazoles occurs at the α-carbon in preference to ring sites.Further reaction of an α-phenyl-2-oxazolemethanol methoxymethyl ether with base and acetyl chloride leads to an acyloin derivative.Chromic acid oxidation is used to prepare both 2- and 4-benzoyloxazoles.The formation of an 2-ethoxyoxazole from 2-oxazolone vis Meerwein salt chemistry is described.