95275-72-2

Upstream product

• 563-83-7 ISOPROPYLAMIDE 
• 16483-98-0 2,3-diphenyl-2H-azirine 
• 10374-29-5 N-benzylidenebenzamide 
• 79-30-1 isobutyryl chloride 
• 78-82-0 Isobutyronitrile 
• 447-31-4 Desyl chloride 

Downstream Products

• 1738-54-1 N-isobutyrylbenzamide 

Relevant academic research and scientific papers

Iron-Catalyzed Cycloaddition of Amides and 2,3-Diaryl-2 H-azirines to Access Oxazoles via C-N Bond Cleavage

A novel and efficient iron-catalyzed cycloaddition reaction using readily available 2,3-diaryl-2H-azirines and primary amides is reported. A wide range of trisubstituted oxazoles could be achieved in good yields with good functional group compatibility. In this transformation, two C-N bonds were cleaed and new C-N and C-O bonds were formed.

Synthesis of Extended Oxazoles III: Reactions of 2-(Phenylsulfonyl)methyl-4,5-diaryloxazoles

2-((Phenylsulfonyl)methyl)-4,5-diphenyloxazole is a useful scaffold for synthetic elaboration at the 2-methylene position thereby affording extended oxazoles. The corresponding α-sulfonyl anion reacts smoothly with diverse alkyl halides giving monoalkylated (47-90%), dialkylated (50-97%), and cyclic (59-93%) products. The reductive desulfonylation of the monoalkylated and selected dialkylated products was optimized with a magnesium/mercuric chloride reagent system and afforded desulfonylated products in the range of 66-97%. The anti-inflammatory Oxaprozin was prepared using the α-sulfonyl carbanion strategy along with optimized desulfonylation.

An efficient synthesis of trisubstituted oxazoles via chemoselective O-acylations and intramolecular Wittig reactions

Preparation of new types of trisubstituted oxazoles is realized via chemoselective O-acylations and intramolecular Wittig reactions with ester functionalities using in situ formed phosphorus ylides as key intermediates. A plausible reaction mechanism for this undiscovered chemistry is also proposed based on the existence of expected and rearranged isomeric oxazoles.

Modular synthesis of tetrasubstituted imidazoles and trisubstituted oxazoles by aldimine cross-coupling

A study was conducted to demonstrate the synthesis of tetrasubstituted imidazoles and trisubstituted oxazoles by aldimine cross-coupling reaction. The method involved 1,2-addition of easily available deprotonated N-monosubstituted α-aminotitriles to aldim

Ceric ammonium nitrate promoted oxidation of oxazoles

The ceric ammonium nitrate promoted oxidations of 4,5-diphenyloxazoles and oxazoles with various substitution patterns have been investigated. This transformation results in the formation of the corresponding imide in good yield and tolerates a wide variety of functional groups and substituents on the oxazole moiety.

Convenient syntheses of 2-alkyl(Aryl)-4,5-diphenyloxazoles and 2-alkyl(Aryl)-4-phepyloxazoles

The synthetic methods to prepare 2-alkyl(aryl)-4,5-diphenyloxazoles and 2-alkyl(aryl)-4-phenyloxazoles were improved on the basis of a mechanistic study of oxazole formation from α-hydroxy ketones (carboxylic esters of benzoin and phenacyl alcohols). By these methods, seven trisubstituted oxazoles and twelve disubstituted oxazoles of the title compounds were prepared.

Base-promoted reactions of α-azido ketones with aldehydes and ketones: A novel entry to α-azido-β-hydroxy ketones and 2,5-dihydro-5-hydroxyoxazoles

The base-promoted reaction of α-azido ketones with aldehydes and ketones provides a new and simple route to either α-azido-β-hydroxy ketones, which are valuable 1,2,3-trifunctionalized synthons, or 2,5-dihydro-5-hydroxyoxazoles, which are a little known type of oxazoline. These two products are formed by the electrophilic trapping of two different anions that are produced sequentially during the reaction. The α-azido-β-hydroxy ketones are formed by an aldol reaction between an enolate of the α-azidoketone and an aldehyde. The 2,5-dihydro-5-hydroxyoxazoles are formed by electrophilic trapping of an imino anion which is produced by nitrogen loss from the α-azido ketone enolate.