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• 1356545-32-8 N-benzyl-N-phenylethynylcarbamic acid benzyl ester 
• 39896-97-4 benzyl-carbamic acid benzyl ester 
• 932-87-6 1-Bromo-2-phenylacetylene 
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• 100-46-9 benzylamine 
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• 1259117-90-2 tert-butyl benzyl(2,2-dibromovinyl)carbamate 
• 98-80-6 phenylboronic acid 

Relevant academic research and scientific papers

Gold and Palladium Mediated Bimetallic Catalysis: Mechanistic Investigation through the Isolation of the Organogold(I) Intermediates

Au-Pd based catalytic systems are a unique couple due to the carbophilic Lewis acidity of Au and the redox properties of Pd. To gain more insight into this bimetallic couple, a synthetic and mechanistic investigation was conducted. As key substrates, ynamides (N-alkynyl allyloxycarbamates and N-alkynyl ethyloxycarbamates) were used. Essential for the mechanistic part was the isolation of the organogold(I) intermediate to validate the proposed mechanism. In total, 18 polysubstituted oxazolones and 12 organogold(I) complexes were synthesized.

An efficient silver tetrafluoroborate-catalyzed cycloisomerization of ynamides

A silver catalyzed-cycloisomerization of N-Boc protected ynamides has been developed under mild reaction conditions to provide a wide range of oxazol-2(3H)-ones in good to excellent yields. Moreover, the acid-promoted Pictet-Spengler cyclization of oxazol

Zinc Chloride Mediated Synthesis of 3H-Oxazol-2-one and Pyrrolo-oxazin-1-one from Ynamide

A simple zinc chloride mediated cyclization of ynamidyl N-carbamates or 2-ynamidyl-(hetero)arylcarboxylates is achieved under mild reaction conditions, leading to the synthesis of useful heterocyclic scaffolds, 3H-oxazol-2-ones and pyrrolo-oxazin-1-ones, with good yields.

Reaction of Ynamides with Iminoiodinane-Derived Nitrenes: Formation of Oxazolones and Polyfunctionalized Oxazolidinones

This article describes the reaction of ynamides with metallanitrenes generated in the presence of an iodine(III) oxidant. N-(Boc)-Ynamides are converted to oxazolones via a cyclization reaction. The reaction is mediated by a catalytic dirhodium-bound nitrene species that first behaves as a Lewis acid. The oxazolones can be converted in a one pot manner to functionalized oxazolidinones following a regio- and stereoselective oxyamination reaction with the same nitrene reagent generated in stoichiometric amounts.

Efficient and Flexible Synthesis of Highly Functionalised 4-Aminooxazoles by a Gold-Catalysed Intermolecular Formal [3+2] Dipolar Cycloaddition

Oxazoles are important motifs within bioactive and functional materials. Complex, fully substituted and functionalised 4-aminooxazoles are accessed by an efficient intermolecular reaction between an ynamide and an N-acylpyridinium N-aminide in the presence of a gold catalyst. The formal [3+2] dipolar cycloaddition employs a nucleophilic nitrenoid approach to access the 1,3-N,O-dipole character in a controllable fashion. The selectivity for a cycloaddition pathway provides a stark contrast against the indiscriminate reactivity of electrophilic acyl nitrenes. Protocols for the formation of acyl-functionalised aminides are reported from accessible precursors including carboxylic esters and acids. The function of these aminides in the oxazole-forming reaction has been explored and it is shown that substantial elaboration is accommodated despite proximity to the reactive centre. As a result functional oxazole-based motifs, such as chiral oxazoles with biologically pertinent substitution patterns, are readily accessible. The use of ynamide types that are unexplored or little used in gold catalysis has been evaluated. Unusual all-heteroatom substitution patterns around the oxazole are shown to be accessible using thio-ynamides. The study shows that a close stoichiometry of reactants is suitable alongside relatively low loadings of the bench-stable precatalysts in practically straightforward multi-mmol scale reactions. The efficiency and flexibility of this regioselective intermolecular preparation is demonstrated in the ready synthesis of oxazoles with substantial structural and functional group variation.

A facile access to 3,5-disubstituted oxazolones featuring a Cu-catalyzed cyclization of N-alkynyl tert-butyl carbamates

Using cheap and readily accessible CuCl as the catalyst, an operationally simple and efficient method for the synthesis of 3,5-disubstituted oxazolones has been realized by the cyclization of N-alkynyl tert-butyl carbamates. The reaction proceeds under mild reaction conditions and shows good functional group compatibility.

Approach to highly functionalized oxazolones by a Pd-catalyzed cyclization of N-alkynyl tert-butyloxycarbamates

A mild and operationally simple approach to highly functionalized oxazolones has been developed, which involves an intramolecular oxypalladation of N-alkynyl tert-butyloxycarbamates, followed by either protonolysis of the alkenyl C-Pd bond to afford 3,5-disubstituted oxazolones or allylation with allyl halides in the presence of Ag2CO3 to generate 3,4,5-trisubstituted oxazolones, respectively.

Synthesis of 2-oxazolones and α-aminoketones via palladium-catalyzed reaction of β,β-dibromoenamides

β,β-Dibromoenamides show two different interesting reactivities based on the choice of R group under the reaction conditions. On the basis of mechanistic studies, both reactions proceed via an intermolecular Suzuki-Miyaura C-C coupling and an intramolecular C-O coupling.

Synthesis of functionalized oxazolones by a sequence of Cu(ll)- And Au(l)-catalyzed transformations

A study concerning a two-step sequence leading to the formation of diversely 1,5-disubstituted oxazolones is described. The mild conditions employed allow the efficient and rapid synthesis of a variety of such compounds via an initial Cu(II)-catalyzed coupling of a bromoalkyne with a secondary tert-butyloxycarbamate followed by a Au(l)-catalyzed cycloisomerization of the N-alkynyl tert-butyloxycarbamates thus obtained.

OXAZOLINONE DERIVATIVES HAVING CYTOSOLIC PHOSPHOLIPASE A2 INHIBITORY ACTIVITY

The present invention relates to a compound represented by the formula wherein a and b are each a carbon atom; a bond between a and b indicates that it is a single bond or a double bond; X is a hydrogen atom, an optionally substituted aryl group, an optionally substitued heteroaryl group, or an optionally substituted aralkyl group; Y is a hydrogen atom, an optionally substituted aryl group, an optionally substituted aralkyl group, or a carboxyl group or related functional groups thereof; and Z is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aralkyl, an optionally substituted arylalkenyl group, an optionally substituted heteroarylalkyl group, an optionally substituted heteroarylalkenyl group, an optionally substituted aryloxyalkyl group, an optionally substituted aralkyloxyalkyl group, an optionally substituted arylcarbonylalkyl group, an optionally substituted arylsulfonylalkyl group, an optionally substituted heteroarylsulfonylalkyl group, an optionally substituted aminoalkyl group, an optionally substituted carboxyalkyl group or related functional groups thereof, an optionally substituted alkyloxycarbonyl group, an optionally substituted aralkyloxycarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted alkylsulfonyl group, an optionally substituted arylsulfonyl group, or an optionally substituted heteroarylsulfonyl group; provided that X, Y and Z are not a hydrogen atom at the same time, and a pharmaceutical composition containing the same. The compounds of the present invention have a cytosolic phospholipase A2 inhibitiory activity.