A novel and efficient synthesis of oxazoles from tosylmethylisocyanide and carbonyl compounds

Photochemistry of 4- and 5- phenyl substituted isoxazoles

“…5-Phenylisoxazole (4) was prepared by reaction of 3-oxo-3-phenylpropionaldehyde oxime with acetyl chloride [33]; 4-methyl-5-phenylisoxazole (10) by reaction of 2-benzoylpropanal with hydroxylamine hydrochloride [34]; 4-phenylisoxazole (22) by condensation of N,N-dimethylformamide and phenylacetic acid in the presence of phosphorus oxychloride [36] and treatment of the resulting 3-(N,N-dimethylamino)-2-phenylpropenal with hydroxylamine hydrochloride [37]; 5-methyl-4-phenylisoxazole (23) by reaction of 3-oxo-2-phenylbutanal with hydroxylamine [35]; 5-phenyl-3-(trifluoromethyl)isoxazole (16) by condensation of 4-phenyl-1,1,1-trifluorobut-3-yne-2-one with hydroxylamine hydrochloride [38]; 3-azido-1-phenylpropen-1-one (41) by reaction of 3-chloro-1-phenyl-2-propen-1-one [39] with sodium azide in methanol [40]; 5-phenyloxazole (5) by reaction of benzaldehyde with tosylmethylisocyanide [41]; 3-phenylisoxazole (6) by reaction of benzhydroximidoyl chloride [42] with triethylamine in the presence of acetylene [43]; 4-phenyloxazole (8) by reaction of α-bromoacetophenone with formamide [44]; 4-methyl-5-phenyloxazole (11), by the reaction of benzaldehyde with α-tosylethylisocyanide [41,44]; cyanophenylacetaldehyde by condensation of benzylcyanide and ethyl formate in the presence of sodium ethoxide [45]; α-benzoylpropionitrile (15) by condensation of propionitrile and methylbenzoate in the presence of sodium methoxide [46]; 2-phenylacetoacetonitrile (26) by condensation of benzylcyanide and ethylacetate in the presence of sodium ethoxide.…”

Synthesis and pharmacological characterization of new tetrahydrofuran based compounds as conformationally constrained histamine receptor ligands

“…Subsequent base-induced [3 + 2]cycloaddition with p-toluenesulfonylmethyl isocyanide (TosMIC) afforded tosyloxazoline 16 as a mixture of diastereomers. 23 The conversion to the corresponding imidazole 17 by treatment with ammonia according to Horne et al turned out to be not feasible. 24 Also several Organic & Biomolecular Chemistry Paper of the silylether, oxidation of alcohol 21 by means of DessMartin periodinane afforded aldehyde 22 which underwent cycloaddition with TosMIC.…”

“…24 Also several Organic & Biomolecular Chemistry Paper of the silylether, oxidation of alcohol 21 by means of DessMartin periodinane afforded aldehyde 22 which underwent cycloaddition with TosMIC. 23 The resulting oxazoline diastereomers 23 were treated with a solution of ammonia in MeOH at elevated temperature in a sealable pressure tube giving rise to the desired imidazole 24 in up to 68% yield. 24 Besides the expected imidazole isomer 24a, epimer 24b was identified as well due to the basic and high temperature conditions applied.…”

“…23 Subsequent reduction with LiAlH 4 furnished alcohol 34. The hydroxy group was converted into a phthalimide moiety via a Mitsunobu reaction.…”

Synthesis and Evaluation of Azole-substituted 2-Aryl-6-methoxy-3,4-dihydronaphthalenes and -naphthalenes as Inhibitors of 17α-Hydroxylase-C17,20-Lyase (P450 17

“…Using a described procedure [17] , the in situ formed compounds 4a and 4b were converted with 1, using the palladium complex Pd(PPh 3 ) 4 as catalyst, to yield compounds 5a and 5b. After deprotection, the aldehydes 6a and 6b were either transformed to the oxazole compounds 7a and 7b using equimolar quantities of tosylmethyl isocyanide (TosMIC) [18] , or were converted to the imidazole derivatives 14a and 14b. For the synthesis of the latter compounds, reaction of the aldehydes 6a and 6b with TosMIC and sodium cyanide to yield the corresponding 4-tosyloxazolines 13a and 13b and subsequent heating of 13a and 13b in saturated methanolic ammonia was performed [19] .…”