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Synlett 2018; 29(01): 106-110
DOI: 10.1055/s-0036-1588564
DOI: 10.1055/s-0036-1588564
letter
New Efficient Synthesis of 1,2,4-Trisubstituted Furans by a Sequential Passerini/Wittig/Isomerization Reaction Starting from Baylis–Hillman β-Bromo Aldehydes
Authors
We gratefully acknowledge the financial support of this work by the National Natural Science Foundation of China (No. 21572075) and the 111 Project B17019.
Further Information
Publication History
Received: 12 June 2017
Accepted after revision: 26 July 2017
Publication Date:
25 August 2017 (online)
Abstract
A new and efficient synthesis of 1,2,4-trisubstituted furans from a Baylis–Hillman β-bromo aldehyde, an acid, an isocyanide, and methyl(diphenyl)phosphine, by a sequential Passerini condensation, Wittig reaction, and isomerization in the presence of triethylamine is reported.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588564.
- Supporting Information (PDF) (opens in new window)
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- 17 1-(Aminocarbonyl)-3-aryl-2-(bromomethyl)prop-2-en-1-yl Esters 4; General Procedure The appropriate acid 2 (2 mmol) and isocyanide 3 (2 mmol) were added to a solution of the Baylis–Hillman β-bromo aldehyde 1 (2 mmol) in CH2Cl2 (4 mL), and the mixture was stirred at r.t. for 3 d until the reaction was complete (TLC). The solvent was removed under reduced pressure, and the residue was purified by flash chromatography [silica gel, EtOAc/PE (1:10)]. (2Z)-2-(Bromomethyl)-1-[(tert-butylamino)carbonyl]-3-(4-nitrophenyl)prop-2-en-1-yl Benzoate(4a) White solid; yield: 664 mg (70%); mp 118–120 °C. 1H NMR (600 MHz, CDCl3): δ = 8.24 (d, J = 7.2 Hz, 2 H, Ar-H), 8.13 (d, J = 5.4 Hz, 2 H, Ar-H), 7.62–7.51 (m, 5 H, Ar-H), 7.07 (s, 1 H, =CH), 6.27 (s, 1 H, NH), 6.03 (s, 1 H, CH), 4.26 (d, J = 10.8 Hz, 1 H, CH2 a), 4.16 (d, J = 10.2 Hz, 1 H, CH2 b), 1.41 (s, 9 H, 3CH3). 13C NMR (150 MHz, CDCl3): δ = 166.0, 164.5, 147.1, 141.5, 135.4, 133.9, 133.3, 129.8, 129.6, 128.7, 123.8, 75.8, 51.8, 28.5, 27.1. HRMS: m/z [M + H]+ calcd for C22H24BrN2O5: 475.0863; found: 475.0860.
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- 21 Furans 5; General Procedure In an oven-dried flask, bromide 4 (1 mmol) and Ph2MeP (0.20 g, 1 mmol) were dissolved in toluene (5 mL) at r.t. After two hours, the white phosphonium salt solid 11 formed. Without isolation of the phosphonium salt intermediate, NEt3 (0.20 g, 2 mmol) was added and the mixture was stirred at reflux for 3–12 h until the reaction was complete (TLC). The solution was then concentrated under reduced pressure and the residue was purified by flash chromatography [silica gel, EtOAc/PE (1:12 to 1:1)]. N-(tert-Butyl)-3-(4-nitrobenzyl)-5-phenyl-2-furamide (5a) Light-yellow oil; yield: 309 mg (82%). 1H NMR (600 MHz, CDCl3): δ = 8.04 (d, J = 8.4 Hz, 2 H, Ar-H), 7.53 (d, J = 7.2 Hz, 2 H, Ar-H), 7.39–7.23 (m, 5 H, Ar-H), 6.37 (s, 1 H, furan-4-H), 6.21 (s, 1 H, NH), 4.31 (s, 2 H, CH2), 1.43 (s, 9 H, 3CH3). 13C NMR (150 MHz, CDCl3): δ = 158.8, 153.5, 147.9, 146.4, 142.0, 130.1, 129.5, 129.2, 128.7, 128.6, 124.3, 123.6, 109.0, 51.4, 31.3, 29.0. HRMS: m/z [M + H]+ calcd for C22H23N2O4: 379.1652; found: 379.1653.