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Synlett 2016; 27(17): 2473-2476
DOI: 10.1055/s-0035-1562602
DOI: 10.1055/s-0035-1562602
letter
Highly Efficient One-Pot Synthesis of Novel Propargylamine-Based Sulfonamides by an A3-Coupling Reaction
Authors
Weitere Informationen
Publikationsverlauf
Received: 12. Mai 2016
Accepted after revision: 28. Juni 2016
Publikationsdatum:
28. Juli 2016 (online)
Abstract
Novel propargylamine-based sulfonamides were synthesized in excellent yields by the copper(I) iodide catalyzed three-component coupling of propargylsulfonamides, morpholine, and aldehydes.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562602.
- Supporting Information (PDF)
-
References and Notes
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- 27 N-Benzyl-N-(4-aryl-4-morpholin-4-ylbut-2-yn-1-yl)-4-toluenesulfonamides (8a–g); General Procedure Morpholine (7; 1 mmol), the appropriate aldehyde 6 (1 mmol), and the appropriate N-propargylsulfonamide 5 (1 mmol) were added to a suspension of CuI (0.1 mmol) and K2CO3 (0.1 mmol) in toluene (4.0 mL), and the mixture was stirred at 110 °C for 48 h. When the reaction was complete (TLC), the product was purified by column chromatography [silica gel, hexane–EtOAc (4:1)]. N-Benzyl-N-(4-morpholin-4-yl-4-phenylbut-2-yn-1-yl)-4-toluenesulfonamide (8a) Yellow oil; yield: 412 mg (87%). 1H NMR (400 MHz, CDCl3): δ = 2.35–2.40 (m, 7 H), 3.68–3.72 (m, 4 H), 4.14–4.20 (ABdd, J = 18.6, 2.0 Hz, 2 H), 4.41 (br s, 1 H), 4.43 (ABd, J = 14.0 Hz, 1 H), 4.48 (ABd, J = 14.0 Hz, 1 H), 7.24 (d, J = 8.0 Hz, 2 H), 7.34–7.40 (m, 10 H), 7.84 (d, J = 6.6 Hz, 2 H). 13C NMR (100 MHz, CDCl3): δ = 21.55, 35.95, 49.69, 50.02, 61.44, 66.90, 80.75, 81.53, 127.78, 127.94, 128.17, 128.23, 128.37, 128.38, 128.73, 128.76, 129.67, 134.99, 136.25, 143.50. N-Benzyl-N-[4-morpholin-4-yl-4-(4-tolyl)but-2-yn-1-yl]-4-toluenesulfonamide (8b) Yellow oil; yield: 405 mg (83%). 1H NMR (400 MHz, CDCl3): δ = 2.33–2.36 (m, 7 H), 2.39 (s, 3 H), 3.68–3.76 (m, 4 H), 4.13–4.19 (ABdd, J = 18.8, 2.0 Hz, 2 H), 4.28–4.35 (br s, 1 H), 4.41 (ABd, J = 14.0 Hz, 1 H), 4.47 (ABd, J = 14.0 Hz, 1 H), 7.15 (d, J = 8.0 Hz, 2 H), 7.21–7.26 (m, 4 H), 7.33–7.40 (m, 5 H), 7.83 (d, J = 8.4 Hz, 2 H). 13C NMR (100 MHz, CDCl3): δ = 21.17, 21.55, 35.97, 49.69, 50.00, 61.20, 66.93, 80.44, 81.85, 127.78, 128.16, 128.30, 128.31, 128.75, 128.91, 129.68, 134.15, 135.02, 136.28, 137.63, 143.47.