25594-98-3

Upstream product

• 6660-08-8 N-(2-(4-chlorophenyl)-2-oxoethyl)acetamide 
• 59009-63-1 methyl N-(tosylmethyl)acetimidate 
• 104-88-1 4-chlorobenzaldehyde 
• 3282-33-5 1-(4-chlorophenyl)-2-diazoethanone 
• 75-05-8 acetonitrile 
• 621-23-8 1,2,3-trimethoxybenzene 
• 80224-43-7 methyl N-(tosylmethyl)acetimidate fluorosulfonate 
• 99-91-2 para-chloroacetophenone 
• 1445-45-0 Trimethyl orthoacetate 
• 5468-33-7 1-(4-chlorophenyl)-2-nitroethan-1-one 
• 873-73-4 4-n-chlorophenylacetylene 

Relevant academic research and scientific papers

A facile one-pot synthesis of 2,5-disubstituted oxazoles using iodobenzene diacetate

A facile one-pot synthesis of oxazoles 1a-h is described that utilizes readily available aromatic α-methyl ketones and a safe hypervalent iodine reagent, iodobenzene diacetate.

A Heterogeneous Gold(I)-Catalyzed [2 + 2 + 1] Annulation of Terminal Alkynes, Nitriles, and Oxygen Atoms Leading to 2,5-Disubstituted Oxazoles

The first heterogeneous gold(I)-catalyzed [2 + 2 + 1] annulation of terminal alkynes, nitriles, and oxygen atoms has been achieved by using an MCM-41-immobilized phosphine-gold(I) complex as catalyst and 8-methylquinoline N-oxide as oxidant under mild conditions, yielding a variety of 2,5-disubstituted oxazoles in good to excellent yields with broad substrate scope. The new heterogeneous gold(I) catalyst can easily be recovered by simple filtration of the reaction solution and recycled for at least eight times without significant loss of activity.

METHOD FOR PRODUCING OXAZOLE COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing an oxazole compound which makes it possible to obtain an oxazole compound inexpensively and safely. SOLUTION: A ketone compound, a nitrile compound, an iodinating agent, an oxidizing agent and an acid catalyst are mixed for a reaction to obtain an oxazole compound. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2016,JPOandINPIT

One-pot preparation of 2,5-disubstituted and 2,4,5-trisubstituted oxazoles from aromatic ketones with molecular iodine, oxone, and trifluoromethanesulfonic acid in nitriles

Alkyl aryl ketones were successfully converted into the corresponding 2,5-disubstituted and 2,4,5-trisubstituted oxazoles in good to moderate yields in a one-pot manner, utilizing iodine, Oxone, and trifluoromethanesulfonic acid in nitriles under transition-metal-free conditions. The present method could be used for the preparation of Oxaprozin from benzyl phenyl ketone and succinonitrile. A possible reaction mechanism was proposed in which the key intermediates were α-iodoalkyl aryl ketones and α-iodosylalkyl aryl ketones.

Various oxidative reactions with novel ion-supported (diacetoxyiodo) benzenes

The oxidation of secondary alcohols and primary alcohols with two novel ion-supported (diacetoxyiodo)benzenes (IS-DIBs) A and B in the presence of a catalytic amount of 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO) in dichloromethane at room temperature proceeded efficiently to provide the corresponding ketones and aldehydes, respectively, in good yields. The oxidative reaction of N,N-diisopropylbenzylamines with those IS-DIBs was also carried out to generate the corresponding aromatic aldehydes in good yields. In addition, the Hofmann rearrangement of primary amides in methanol under basic conditions and the oxidative 1,2-rearrangement of propiophenones in trimethyl orthoformate under acidic conditions with those IS-DIBs provided the corresponding methyl carbamates and methyl 2-arylpropanoates, respectively, in good yields. Moreover, treatment of acetophenones with those IS-DIBs in the presence of trifluoromethanesulfonic acid in acetonitrile generated the corresponding 5-aryl-2-methyloxazoles in good yields. In those five reactions, the desired products were obtained in good yields with high purity by simple extraction of the reaction mixture with diethyl ether and subsequent removal of the solvent from the extract. Moreover, ion-supported iodobenzenes, which were the co-products derived from IS-DIBs in the present oxidative reactions, were recovered in good yields and could be re-oxidized to IS-DIBs A and B for reuse in the same oxidative reactions.

Synthesis of highly substituted oxazoles through iodine(III)-mediated reactions of ketones with nitriles

In the presence of trifluoromethanesulfonic acid (TfOH) or bis(trifluoromethanesulfonyl) imide (Tf2NH), iodosobenzene (PhI=O) efficiently promoted the reactions of dicarbonyl compounds as well as monocarbonyl compounds with nitriles to give 2,4-disubstituted and 2,4,5-trisubstituted oxazole in a single step under the mild conditions.

Iron-promoted practical one-pot synthesis of 2,5-disubstituted oxazoles

A practical one-pot protocol for the synthesis of 2,5-disubstituted oxazoles from 1-aryl-2-nitroethanones was reported. In the presence of iron/AcOH in acetonitrile, the reaction of 1-aryl-2-nitroethanones with trimethyl orthoacetate or trimethyl orthobenzoate delivered the corresponding 2,5-disubstituted oxazoles in moderate to good yields. Copyright

Iodoarene-catalyzed one-pot preparation of 2,4,5-trisubstituted oxazoles from alkyl aryl ketones with mCPBA in nitriles

2,4,5-Trisubstituted oxazoles could be easily prepared in moderate yields by the reaction of alkyl aryl ketones, iodoarene, m-chloroperbenzoic acid, and trifluoromethanesulfonic acid in acetonitrile, propionitrile, butyronitrile, and isobutyronitrile, res

Iodoarene-mediated one-pot preparation of 2,5-disubstituted and 2,4,5-trisubstituted oxazoles from alkyl aryl ketones with oxone in nitriles

The reaction of alkyl aryl ketones with Oxone and trifluoromethanesulfonic acid in the presence of iodoarene in acetonitrile, propionitrile, butyronitrile, and isobutyronitrile, provided directly the corresponding 2,5-disubstituted and 2,4,5-trisubstituted oxazoles, respectively, in moderate yields. Here, reactive aryliodonium I(III) species is formed in situ by the reaction of iodoarene with Oxone and trifluoromethanesulfonic acid, and the formed aryliodonium I(III) species reacts with alkyl aryl ketone to generate β-keto iodonium species. Then, β-keto iodonium species reacts with nitrile to produce the corresponding oxazole. In principle, iodoarene works as a catalyst. However, 1 equiv of iodoarene is required because 1 equiv of reactive aryliodonium I(III) species must be formed before the reaction with alkyl aryl ketone.

Iodoarene-mediated one-pot preparation of 2,4,5-trisubstituted oxazoles from ketones

2-Methyl-5-aryloxazole and 2-ethyl-5-aryloxazole derivatives were smoothly and efficiently obtained in one-pot manner from alkyl aryl ketones with iodoarene, m-chloroperbenzoic acid, and trifluoromethanesulfonic acid in acetonitrile and propionitrile, res