Reaction between Chalcones, 1,3-Dicarbonyl Compounds, and Elemental Sulfur: A One-Pot Three-Component Synthesis of Substituted Thiophenes

Mehdi Adib; Saideh Rajai-Daryasarei; Rahim Pashazadeh; Mehdi Jahani; Massoud Amanlou

doi:10.1055/s-0037-1610147

Synlett, Inhaltsverzeichnis

Synlett 2018; 29(12): 1583-1588
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

Mehdi Adib*

^aSchool of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran eMail: madib@khayam.ut.ac.ir

,

Saideh Rajai-Daryasarei

^aSchool of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran eMail: madib@khayam.ut.ac.ir

,

Rahim Pashazadeh

^aSchool of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran eMail: madib@khayam.ut.ac.ir

,

Mehdi Jahani

^aSchool of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran eMail: madib@khayam.ut.ac.ir

,

Massoud Amanlou

^bPharmaceutical Sciences Research Center and Department of Medicinal Chemistry, Tehran University of Medical Sciences, Tehran, Iran

› Institutsangaben

Abstract

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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 compounds

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Referenzen

References and Notes

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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.

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