One-Pot Synthesis of 2,4,5-Trisubstituted Oxazoles via a Tandem Passerini Three-Component Coupling/Staudinger/Aza-Wittig/Isomerization Reaction

Abstract

2,4,5-Trisubstituted oxazoles were prepared via a tandem Passerini three-component coupling/Staudinger/aza-Wittig/isomerization reaction in one-pot fashion, starting from easily accessible α-azidocinnamaldehydes, acids, isocyanide and triphenylphosphine.

Key words

oxazole - tandem reaction - aza-Wittig reaction - ­Passerini reaction - isomerization

• References and Notes

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• 19 General Procedure for the Preparation of Oxazoles 5: A mixture of α-azidocinnamaldehyde 1 (0.17 g, 1 mmol), isocyanide (1 mmol), and acid (1 mmol) was stirred in CH₂Cl₂ (5 mL) at r.t. or at 40–50 °C for 24–48 h. Then Ph₃P (0.26 g, 1 mmol) in CH₂Cl₂ (5 mL) was added dropwise to the reaction system and the reaction mixture was stirred at r.t. for 2 h. The solvent was evaporated under reduced pressure, and toluene (10 mL) was added. After the resulting solution was refluxed for 8–10 h, solid K₂CO₃ (0.014 g, 0.1 mmol) was added to the reaction system and the solution was refluxed for further 1–2 h. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel (Et₂O–petroleum ether, 1:6) to give oxazoles 5. 5a: white solid; mp 145–146 °C. ¹H NMR (600 MHz, CDCl₃): δ = 8.03 (d, J = 7.2 Hz, 2 H, ArH), 7.18–7.45 (m, 7 H, ArH), 6.08 (s, 1 H, NH), 4.34 (s, 2 H, CH₂), 1.50 (s, 9 H, 3 × Me). ¹³C NMR (150 MHz, CDCl₃): δ = 159.8, 157.6, 145.4, 139.4, 138.6, 131.1, 129.0, 128.7, 128.3, 126.8, 126.5, 126.3, 51.7, 32.8, 29.0. MS (EI, 70 eV): m/z (%) = 334 (87) [M⁺], 278 (86), 261 (33), 131 (100), 103 (39). Anal. Calcd for C₂₁H₂₂N₂O₂: C, 75.42; H, 6.63; N, 8.38. Found: C, 75.56; H, 6.73; N, 8.59.