Novel Syntheses of N-Aryloxazolidin-2-ones via Tandem Reactions of Vinyl Sulfonium Salts

Abstract

An unprecedented and efficient domino reaction of diphenyl vinyl sulfonium salt with carbamates leading to the syntheses of N-aryloxazolidin-2-ones has been developed. The scope of this transformation has been studied and a plausible mechanism has been proposed.

Key words

N-aryloxazolidin-2-one - tandem reaction - vinyl sulfonium - carbamate

References and Notes

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14

Typical Procedure for the Tandem Reactions - Synthesis of 3-Phenyloxazolidin-2-one
tert-Butyl phenylcarbamate (96 mg, 0.5 mmol) and Et₃N (152 mg, 1.5 mmol) were charged into an oven-dried flask, followed by the addition of CH₂Cl₂ (2 mL) under the protection of nitrogen atmosphere to form a solution. The solution of diphenyl vinyl sulfonium triflate (543 mg, 1.5 mmol) in CH₂Cl₂ (3 mL) was added into the above solution by syringe under N₂ at r.t. The reaction mixture was then put into a 45 ˚C oil bath to react for 24 h. After the completion of reaction, the solvent was removed under reduced pressure. The residue was then separated on a silica gel column by using PE-EtOAc (1:2) as eluent, and the final product was obtained as pale yellow powder (42 mg, 52%). ^¹H NMR (400 MHz, CDCl₃, TMS): δ = 7.51 (d, J = 8.0 Hz, 2 H), 7.36 (t, J = 8.0 Hz, 2 H), 7.12 (t, J = 7.4 Hz, 1 H), 4.42 (t, J = 8.0 Hz, 2 H), 3.99 (t, J = 8.0 Hz, 2 H). ^¹³C NMR (100 MHz, CDCl₃): δ = 155.3, 138.3, 129.1, 124.1, 118.2, 61.3, 45.2. HRMS (EI): m/z calcd for C₉H₉NO₂ [M]⁺: 163.0633; found: 163.0627.