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Relevant academic research and scientific papers

Iodine catalysed intramolecular C(sp3)-H functionalization: synthesis of 2,5-disubstituted oxazoles from N-arylethylamides

Iodine catalyzed synthesis of 2,5-disubstituted oxazoles from N-arylethylamides through intramolecular C(sp3)-H functionalization under metal-free conditions is described. The method is tolerable to a wide range of substrates having a variety of functional groups with moderate to good yields of the products.

One-pot conversion of amino acids into 2,5-disubstituted oxazoles: No metals needed

2,5-Disubstituted oxazoles with a variety of alkyl and aryl groups are efficiently formed from N-acylamino acids, by a one-pot radical decarboxylation- oxidation-enolization and iodine-promoted cyclization process. Remarkably, the reaction takes place under mild conditions, and no metal catalysis is needed. The process can be useful for the direct modification of small peptides.

Room temperature copper(II)-catalyzed oxidative cyclization of enamides to 2,5-disubstituted oxazoles via vinylic C-H functionalization

A copper(II)-catalyzed oxidative cyclization of enamides to oxazoles via vinylic C-H bond functionalization at room temperature is described. Various 2,5-disubstituted oxazoles bearing aryl, vinyl, alkyl, and heteroaryl substituents could be synthesized in moderate to high yields. This reaction protocol is complementary to our previously reported iodine-mediated cyclization of enamides to afford 2,4,5-trisubstituted oxazoles.

Copper(ii)-mediated oxidative cyclization of enamides to oxazoles

The copper(ii)-mediated oxidative cyclization of enamides to oxazoles is reported. A range of 2,5-disubstituted oxazoles were prepared in moderate to good yields in two steps from simple amide and alkyne precursors.

A domino copper-catalyzed C-N and C-O cross-coupling for the conversion of primary amides into oxazoles

A variety of oxazoles can efficiently be prepared, in a single step and in good yield, from primary amides and 1,2-dihaloalkenes using copper-catalysis. This new method allows the regioselective formation of a range of substituted oxazoles. The required 1,2-dihaloalkenes can prepared by simple treatment of alkynes with elemental bromine or iodine. Georg Thieme Verlag Stuttgart.

LITHIATED 2-METHYL-5-PHENYLOXAZOLES, FORMATION AND REACTIONS WITH ELECTROPHILES

The methyl group of 2-methyl-5-phenyloxazole (1) has been lithiated with lithium diisopropylamide (LDA) and the resulting lithio derivative has been reacted with electrophiles to obtain 2-alkyl-5-phenyloxazoles.

Lewis Acid Promoted Reactions of Diazocarbonyl Compounds. 3. Synthesis of Oxazoles from Nitriles through Intermediate β-Imidatoalkenediazonium Salts

Lewis acid promoted reactions of α-diazocarbonyl compounds with nitriles provide a general method for the production of oxazoles in high isolated yields.The generality of this method is evaluated by the effectiveness of oxazole formation in surveys of Lewis acids, diazocarbonyl compounds, and nitriles.Because of the relative absence of α-halogenation products in reactions performed with BF3*Et2O, this Lewis acid is preferred when the nitrile is employed as the reaction solvent.Reactions of diazo ketones in nitrile solvents generally result in higher oxazole yields(70-99percent) than do reactions of ethyl diazoacetate (26-31percent).When these transformations are performed at or below room temperature, at least 1 equiv of the Lewis acid is required, although catalytic activity is observed in reactions performed at 65 deg C.In BF3*Et2O promoted reactions, a minimum tenfold molar excess of nitrile is required for optimum oxazole production, although use of SbF5 results in high yields of oxazoles even when only a threefold excess of the nitrile is employed.The mechanism for oxazole formation is established as involving initial activation of the nitrile through association with the Lewis acid, followed by attack of the nitrilium complex at the carbonyl oxygen of the diazocarbonyl compound and internal displacement of nitrogen.Although Lewis acid association with the diazocarbonyl compound is the more favorable process in reactions performed with equivalent amounts of nitrile and diazocarbonyl compound, only equilibrium association of the Lewis acid with the nitrile effectively leads to oxazole formation.