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Synlett 2018; 29(12): 1583-1588
DOI: 10.1055/s-0037-1610147
DOI: 10.1055/s-0037-1610147
letter
Reaction between Chalcones, 1,3-Dicarbonyl Compounds, and Elemental Sulfur: A One-Pot Three-Component Synthesis of Substituted Thiophenes
Further Information
Publication History
Received: 22 February 2018
Accepted after revision: 19 April 2018
Publication Date:
05 June 2018 (online)
Abstract
A simple and atom-economic synthesis of highly substituted thiophenes is demonstrated. Heating a solution of a chalcone and a linear/cyclic 1,3-dicarbonyl compound with elemental sulfur in CH3CN in the presence of NEt3 at 80 °C afforded the corresponding substituted thiophenes in good to excellent yields.
Key words
multi-component reactions - substituted thiophenes - sulfur - chalcones - 1,3-dicarbonyl compoundsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610147.
- Supporting Information
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- 14 Representative Procedure for the Synthesis of 3-Acetyl-4-benzoyl-2-methyl-3-phenyl thiophene (4a) A mixture of 1,3-diphenyl-2-propen-1-one (1a) (0.208 g, 1.0 mmol), 2,4-pentanedione (2a) (0.100 g, 1.0 mmol), and triethylamine (0.025 g 0.25 mmol) in CH3CN (1 mL) was stirred at 80 °C for 12 h. Subsequently, triethylamine (0.071 g, 0.7 mmol) and elemental sulfur (0.038 g, 1.2 mmol) were added to the mixture, which was heated to 80 °C for a further 5 h. After completion of the reaction, as indicated by TLC monitoring, the mixture was cooled to ambient temperature and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography by using n-hexane/EtOAc (8:1 v/v) as the eluent to afford the desired product 4a. 3-Acetyl-5-benzoyl-2-methyl-4-phenylthiophene (4a) White solid. Yield: 0.269 g, 84%. Mp 60–62 °C. IR (KBr) (ν max/cm–1): 1682 and 1622 (C=O), 1520, 1488, 1445, 1363, 1301, 1234, 1171, 1113, 1073, 1028, 963, 904, 869, 786, 721, 696, 656, 621. EI-MS: m/z (%) = 320 (100) [M]+, 305 (33), 277 (8), 243 (7), 227 (30), 215 (7), 201 (19), 171 (19), 121 (11), 105 (78), 77 (67), 43 (21). 1H NMR (500.1 MHz, CDCl3): δ = 1.80 (s, 3 H, CH3), 2.60 (s, 3 H, CH3), 7.09–7.16 (m, 7 H, 7 CH), 7.30 (t, 1 H, J = 7.4 Hz, CH), 7.50 (dd, 2 H, J = 8.2, 1.2 Hz, 2 CH) ppm. 13C NMR (125.8 MHz, CDCl3): δ = 15.36 and 31.21 (2 CH3), 127.95 (2 CH), 128.39 (CH), 128.42 (2 CH), 129.53 (2 CH), 129.79 (2 CH), 132. 36 (C H), 135.03, 135.32, 137.77, 141.40, 145.04 and 148.29 (6 C), 189.84 and 199.80 (2 C=O) ppm. Anal. Calcd for C20H16O2S (320.41): C, 74.97; H, 5.03; S, 10.01. Found: C, 74.83; H, 4.86; S, 10.13.