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Synlett 2014; 25(5): 721-723
DOI: 10.1055/s-0033-1340596
DOI: 10.1055/s-0033-1340596
letter
One-Pot Synthesis of 2,4,5-Trisubstituted Oxazoles via a Tandem Passerini Three-Component Coupling/Staudinger/Aza-Wittig/Isomerization Reaction
Further Information
Publication History
Received: 31 October 2013
Accepted after revision: 10 December 2013
Publication Date:
14 January 2014 (online)
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.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
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.