four.65; H, four.07; N, 3.41. Mp 105 (decomp) N-(3-(4-Chlorophenyl)-3-oxoprop-1-ynyl)-N-phenyl-4-tolylsulfonamide, 4. The reaction with 4-chlorobenzoyl chloride (31.4 mg, 0.18 mmol) plus the ynamide (32.five mg, 0.12 mmol) was performed at 30 for 20 h. The concentrated crude residue was purified by column chromatography (two:1 dichloromethane/hexanes) to provide 47 mg (0.115 mmol, 96 ) of a white strong. 1H NMR (400 MHz): eight.09 (d, J = eight.six Hz, 2H), 7.57 (d, J = 8.4 Hz, 2H), 7.45 (d, J = eight.5 Hz, 2H), 7.39-7.28 (m, 3H), 7.28-7.18 (m, 4H), 2.39 (s, 3H). 13C NMR (one hundred MHz): 175.4, 146.0, 140.two, 137.0, 135.4, 132.9, 130.5, 129.9, 129.5, 129.3, 128.9, 128.1, 126.4, 90.7, 74.7, 21.six. Anal. Calcd For C22H16ClNO3S: C, 64.47; H, three.93; N, three.42. Identified: C, 64.38; H, 4.05; N, three.46. Mp 105-107 . N-(3-(4-Cyanophenyl)-3-oxoprop-1-ynyl)-N-phenyl-4-tolylsulfonamide, five. The reaction with 4-cyanobenzoyl chloride (30.0 mg, 0.18 mmol) and also the ynamide (32.7 mg, 0.12 mmol) was performed at 30 for 18 h. The concentrated crude residue was purified by column chromatography (three:1 dichloromethane/hexanes) to offer 46.five mg (0.116 mmol, 97 ) of a white solid. 1H NMR (400 MHz): 8.29 (d, J = eight.three Hz, 2H), 7.82 (d, J = 8.1 Hz, 2H), 7.60 (d, J = eight.3 Hz, 2H), 7.47-7.34 (m, 3H), 7.29 (d, J = 8.Josiphos SL-J009-1 Pd G3 Chemscene 1 Hz, 2H), 7.Buy2413767-30-1 27-7.23 (m, 2H), two.43 (s, 3H). 13C NMR (100 MHz): 174.8, 146.two, 139.eight, 136.eight, 136.7, 132.eight, 132.four, 130.0, 129.6, 129.4, 128.1, 126.4, 117.9, 116.eight, 92.3, 75.1, 21.7. Anal. Calcd For C23H16N2O3S: C, 68.98; H, four.03; N, 7.00. Located: C, 68.67; H, 4.14; N, 6.92. Mp 155 (decomp) N-(3-(2-Naphthyl)-3-oxoprop-1-ynyl)-N-phenyl-4-tolylsulfonamide, 6. The reaction with 2-naphthoyl chloride (35.0 mg, 0.18 mmol plus the ynamide (32.9 mg, 0.121 mmol) was performed at 30 for 12 h. The concentrated crude residue was purified by column chromatography (1:1 dichloromethane/hexanes) to provide 51.five mg (0.12 mmol, 99 ) of a white strong. 1H NMR (400 MHz): 8.88 (s, 1H), eight.19 (dd, J = 8.six, 1.7 Hz, 1H), 8.06 (d, J = 8.1 Hz, 1H), 7.94 (d, J = 8.7 Hz, 1H), 7.91 (d, J = 8.0 Hz, 1H), 7.65 (d, J = eight.PMID:24025603 two Hz, 2H), 7.65-7.54 (m, 2H), 7.44-7.34 (m, 3H), 7.35-7.27 (m, 2H), 7.28-7.22 (m, 2H), 2.41 (s, 3H). 13C NMR (100 MHz): 176.8, 145.9, 137.1, 135.9, 134.5, 132.9, 132.six, 132.five, 130.0, 129.9, 129.five, 129.2, 128.8, 128.four, 128.1, 127.eight, 126.8, 126.6, 123.six, 90.two, 75.0, 21.7. Anal. Calcd For C26H19NO3S: C, 73.39; H, 4.50; N, 3.29. Discovered: C, 73.32; H, 4.77; N, 3.32. N-(3-(1-Naphthyl)-3-oxoprop-1-ynyl)-N-phenyl-4-tolylsulfonamide, 7. The reaction with 1-naphthoyl chloride (55.0 mg, 0.dx.doi.org/10.1021/jo500365h | J. Org. Chem. 2014, 79, 4167-The Journal of Organic Chemistrymmol) as well as the ynamide (54.five mg, 0.20 mmol) was performed at 20 for 38 h. The concentrated crude residue was purified by column chromatography (1:1 dichloromethane/hexanes) to offer 67 mg (0.16 mmol, 79 ) of a colorless oil. 1H NMR (400 MHz): 9.21 (d, J = eight.five Hz, 1H), eight.56 (d, J = 7.1 Hz, 1H), 8.06 (d, J = 8.2 Hz, 1H), 7.89 (d, J = eight.1 Hz, 1H), 7.68-7.57 (m, 4H), 7.54 (dd, J = 7.six, 7.4 Hz, 1H), 7.41- 7.33 (m, 3H), 7.32-7.26 (m, 2H), 7.23 (d, J = 8.1 Hz, 2H), 2.38 (s, 3H). 13C NMR (100 MHz): 178.7, 145.9, 137.2, 134.6, 134.0, 133.9, 132.8, 132.7, 130.7, 129.9, 129.5, 129.two, 128.7, 128.five, 128.two, 126.6, 126.5, 125.9, 124.7, 88.7, 76.0, 21.7. Anal. Calcd For C26H19NO3S: C, 73.39; H, 4.50; N, three.29. Found: C, 73.30; H, four.89; N, 3.30. N-(four,4-Dimethyl-3-oxopent-1-ynyl)-N-phenyl-4-tolylsulfonamide, 8. The reaction with pivaloyl chloride (21.6 mg, 0.179 mmol).