2021
DOI: 10.1021/acs.joc.1c02276
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PIFA-Mediated Tandem Hofmann-Type Rearrangement and Cyclization Reaction of α-Acyl-β-aminoacrylamides: Access to Polysubstituted Oxazol-2(3H)-ones

Abstract: An efficient and straightforward synthesis of polysubstituted oxazol-2­(3H)-ones has been developed via a tandem Hofmann-type rearrangement and cyclization reaction of various α-acyl-β-aminoacrylamides mediated by phenyl iodine­(III) bis­(trifluoroacetate) (PIFA) in the presence of trifloroacetic acid (TFA). This novel protocol features readily available starting materials, mild reaction conditions, simple execution, high chemoselectivity, good functional group tolerance, and a metal-free oxidation process.

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Cited by 3 publications
(4 citation statements)
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“…On the basis of the obtained results together with the reported mechanistic studies of Hofmann‐type rearrangement reactions of amides mediated by hypervalent iodine reagents, [24,28] a proposed mechanism for the oxidative cyclization of acetyl amide 1 with cyclic amidine 2 is depicted in Scheme 3. Initially, amidine 2 reacts with PhIO in DCM at room temperature to generate an iminium ion A [29] .…”
Section: Resultsmentioning
confidence: 85%
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“…On the basis of the obtained results together with the reported mechanistic studies of Hofmann‐type rearrangement reactions of amides mediated by hypervalent iodine reagents, [24,28] a proposed mechanism for the oxidative cyclization of acetyl amide 1 with cyclic amidine 2 is depicted in Scheme 3. Initially, amidine 2 reacts with PhIO in DCM at room temperature to generate an iminium ion A [29] .…”
Section: Resultsmentioning
confidence: 85%
“…Surprisingly, no desired product 5 aa was even detectable in the above three cases. These results suggested that the oxidativity of hypervalent iodine reagents and their loading dosages had significant influences on the oxidative reaction of 1 a and DBU [17–24] . The solvent screening revealed that the reaction of 1 a and DBU could also take place in acetonitrile, DMF, ethanol, dioxane or toluene, but the conversion of 1 a was slightly slow and the yield of 5 aa became lower (entries 8–12).…”
Section: Resultsmentioning
confidence: 99%
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