ࡱ> npmM abjbj==WWw0l&&&&NNNb L, $b6.\ \ \ \ \ K K K +++++++$,/ L1+=NK G K K K +}&&\ \ -}}}K &\ N\ +}K +}D}u(lTN*\ P dfb~ n)**.06. * 2e 2*}bb&&&& Melting points were determined with a Bchi B-545 apparatus and are uncorrected. N-Propargylamides were prepared from propargylamine and acyl chlorides or carboxylic acid anhydrides according to standard methods. All of the other reagents, ligands and Pd2(dba)3 are commercially available and were used as purchased, without further purification. Reaction products were purified on axially compressed columns, packed with SiO2 25-40 mm (Macherey Nagel), connected to a Gilson solvent delivery system and to a Gilson refractive index detector, and eluting with n-hexane/ethyl acetate mixtures. 1H NMR (200 MHz) and 13C NMR (50.3 MHz) spectra (CDCl3; TMS as internal standard) were recorded with a Bruker AM 200 spectrometer. IR spectra were recorded with a JASCO FT/IR-430 spectrometer. N-propargylamides N-propargylbenzamide; mp: 107-8; IR (KBr): 3293, 1640 cm-1. 1H NMR d 2.27 (t, J = 2.5 Hz 1H) , 4.27 (dd, J1 = 6.0 Hz, J2 = 2.5 H, 1H), 6.57 (bs, 1H), 7.38-7.54 (m, 3H), 8.01-8.05 (m, 2H). 13CNMR d 29.0, 71.3, 78.3, 127.6, 127.8, 131.3, 136.5, 162.5. Anal calc d for C10H9NO: C, 75.75; H, 5.70; N, 8.80. Found C, 75.81; H, 5.71; N, 8.78. N-propargyl-(4-methyl)benzamide; mp: 115-6; IR (KBr): 3304, 1638 cm-1. 1H NMR d 2.24 (t, J = 2.5 Hz 1H) , 2.36 (s, 3H), 4.20 (dd, J1 = 5.2 Hz, J2= 2.5 Hz, 1H), 6.63 (bs, 1H), 7.18 (d, J = 2.8 Hz, 2H), 7.68 (d, J = 2.8 Hz, 2H)). 13CNMR d 20.9, 29.0, 71.3, 78.3, 127.2, 128.7, 135.6, 141.9, 162.5. Anal calc d for C11H11NO: C, 76.28; H, 6.40; N, 8.09. Found C, 76.35; H, 6.42; N, 8.07. N-propargyl-(4-methoxy)benzamide; mp: 130-1; IR (KBr): 3263, 1642 cm-1. 1H NMR d 2.27 (t, J = 2.5 Hz 1H) , 3.85 (s, 3H), 4.24 (dd, J1 = 5.2 Hz, J2 = 2.5 H, 1H), 6.38 (bs, 1H), 7.68 6.89-6.94 (m, 2H), 7.74-7.78 (m, 2H). 13CNMR d 29.7, 55.4, 71.7, 79.9, 113.8, 126.0, 128.9, 162.4, 166.6. Anal calc d for C11H11NO2: C, 69.83; H, 5.86; N, 7.40. Found C, 69.77; H, 5.88; N, 7.42. N-propargyl-(3-trifluoromethyl)benzamide; mp: 105-6; IR (KBr): 3354, 1643 cm-1. 1H NMR d 2.31 (t, J = 2.5 Hz 1H), 4.28 (dd, J1 = 5.4 Hz, J2 = 2.6 H, 1H), 6.50 (bs, 1H), 7.54-7.62 (m, 1H), 7.76-7.80 (m, 1H), 7.96-8.05 (m, 2H). 13CNMR d 30.0, 72.3, 79.1, 124.5 (q, J = 272.6 Hz), 125.0 (q, 3.8 Hz), 129.3 (q, 3.7 Hz), 130.2, 131.3 (q, J = 1.3 Hz), 132.1 (q, J = 32.8 Hz ), 135.5, 166.8; 19FNMR (CHCl3) d -63.2. Anal calc d for C11H8F3NO: C, 58.15; H, 3.55; N, 6.17. Found C, 58.21; H, 3.54; N, 6.19. N-1-(1-ethynylcycloexyl)benzamide; mp: 104-5; IR (KBr): 3290, 1639 cm-1. 1H NMR d 1.40-2.01 (m, 10H), 4.27 (dd, J1 = 6.0 Hz, J2 = 2.5 H, 1H), 5.51(bs, 1H), 7.22-7.54 (m, 5H). 13CNMR d 22.6, 25.4, 37.3, 52.0, 71.7, 86.0, 127.2, 127.6, 131.6, 137.3, 166.0. Anal calc d for C15H17NO: C, 79.26; H, 7.54; N, 6.16. Found C, 79.20; H, 7.52 ; N, 6.18. N-propargyltrifluoroacetamide; mp: oil; IR (neat): 3307, 1714 cm-1. 1H NMR d 2.35 (t, J = 2.6 Hz, 1H), 4.17 (dd, J1 = 6.0 Hz, J2 = 2.6 H, 1H), 7.21 (bs, 1H). 13CNMR d 29.6, 72.9, 77.0, 115.1 (q, J = 287.7Hz), 157.1 (q, J = 37.7Hz).s Anal calc d for C5H4F3NO: C, 39.75; H, 2.67; N, 9.27. Found C, 39.70; H, 2.68; N, 9.28. 2,5-Disubstituted Oxazoles (Table 2, entry 1) 2-Phenyl-5-(2-methylbenzyl)oxazole; mp: oil; IR (neat): 2840, 828, 711, 691 cm-1. 1H NMR d 2.34 (s, 3H), 4.00 (s, 2H), 6.75 (s, 1H), 7.17- 7.32 (m, 4H), 7.37-7.40 (m, 3H), 7.96-8.00 (m, 2H). 13CNMR d 19.3, 29.8, 124.8, 125.9, 126.0, 126.3, 127.2, 127.7, 128.7, 129.5, 130.0, 130.4, 134.8, 136.3, 151.0. Anal calc d for C17H15NO: C, 81.90; H, 6.06; N, 5.62. Found C, 81.82; H, 6.04; N, 5.61. (Table 2, entry 2) 2-(4-Methoxyphenyl)5-(2-methybenzyl)oxazole; mp: oil; IR (neat): 2840, 822 cm-1. 1H NMR d 2.34 (s, 3H), 3.80 (s, 3H), 3.99 (s, 2H), 6.70 (s, 1H), 6.89-6.94 (m, 2H), 7.17-7.40 (m, 4H), 7.89-7.93 (m, 2H). 13CNMR d 19.4, 55.3, 114.1, 120.5, 124.5, 126.2, 127.1, 127.5, 127.6, 129.5, 130.4, 134.9, 136.3, 150.3, 161.0, 161.2. Anal calcd for C18H17NO2: C, 77.40; H, 6.13; N, 5.01. Found C, 77.47; H, 6.10; N, 5.03. (Table 2, entry 3) 2-Phenyl-5-(3-methylbenzyl)oxazole; mp: oil; IR (neat): 2837, 830, 711, 691 cm-1. 1H NMR d 2.32 (s, 3H), 3.99 (s, 2H), 6.85 (s, 1H), 7.00-7.15 (m, 3H), 7.16-7.20 (m, 1H), 7.35-7.42 (m, 3H), 7.96-8.01 (m, 2H). 13CNMR d 21.7, 32.0, 124.8, 125.7, 125.9, 126.1, 127.6, 127.7, 128.6, 128.7, 129.4, 130.0, 136.6, 138.3, 151.5. Anal calc d for C17H15NO: C, 81.90; H, 6.06; N, 5.62. Found C, 81.98; H, 6.08; N, 5.64. (Table 2, entry 4) 2-(4-Methoxyphenyl)-5-(3-methylbenzyl)oxazole; mp: oil; IR (neat): 2835, 835 cm-1. 1H NMR d 2.36 (s, 3H), 3.84 (s, 3H), 4.02 (s, 2H), 6.84 (s, 1H), 6.96 (d, J = 8.3 Hz, 2H), 7.12-7.24 (m, 4H), 7.96 (d, J = 8.3 Hz, 2H). 13CNMR d 21.4, 32.0, 55.3, 114.1, 120.6, 124.5, 125.7, 127.6, 127.7, 128.5, 129.4, 136.7, 138.3, 150.9, 161.1, 161.3. Anal calc d for C18H17NO2: C, 77.40; H, 6.13; N, 5.01. Found C, 77.34; H, 6.15; N, 5.03. (Table 2, entry 5) 2-Phenyl-5-(4-methylbenzyl)oxazole; mp: oil; IR (neat): 2835, 820, 710, 695 cm-1. 1H NMR d 2.31 (s, 3H), 3.98 ((s, 3H), 6.82 (s, 1H); 7.07-7.15 (m, 4H), 7.30-7.43 (m, 2H). 13CNMR d 21.0, 31.7, 124.7, 126.0, 127.7, 128.5, 129.3, 129.5, 133.5, 136.4, 151.6, 161.1. Anal calc d for C17H15NO: C, 81.90; H, 6.06; N, 5.62. Found C, 81.97; H, 6.08; N, 5.61. (Table 2, entry 6) 2-Phenyl-5-(3,5-dimethylbenzyl)oxazole; mp: oil; IR (neat): 2835, 815, 712, 690 cm-1. 1H NMR d 2.28 (s, 6H), 3.95 (s, 2H), 6.85-6.88 (m, 4H), 7.37-7.41 (m, 3H), 7.97-8.01 (m, 2H). 13CNMR d 21.2, 31.9, 124.8, 125.9, 126.1, 126.5, 127.7, 128.5, 129.9, 136.5, 138.2, 151.6, 161.1. Anal calc d for C18H17NO: C, 82.10; H, 6.51; N, 5.32. Found C, 82.03; H, 6.52; N, 5.33. (Table 2, entry 7) 2-Phenyl-5-(3-methoxybenzyl)oxazole; mp: oil; IR (neat): 2835, 832, 711, 691 cm-1. 1H NMR d 3.78 (s, 3H), 4.03 (s, 2H), 6.78-6.88 (m, 4H), 7.21-7.45 (m, 4H), 7.97-8.02 (m, 2H). 13CNMR d 32.1, 55.2, 112.2, 114.5, 121.0, 124.9, 126.1, 127.7, 128.7, 129.7, 130.0, 138.2. 151.2, 159.8, 161.3. Anal calc d for C17H15NO2: C, 76.96; H, 5.70; N, 5.28. Found C, 77.03; H, 5.71; N, 5.29. (Table 2, entry 8) 2-(4-Methoxyphenyl)-5-(3-methoxybenzyl)oxazole; mp: oil; IR (neat): 2835, 825 cm-1. 1H NMR d 3.76 (s, 3H), 3.80 (s, 3H), 3.99 (s, 2H), 6.77-6.94 (m, 6H), 7.19-7.23 (m, 1H), 7.89-7.94 (m, 2H). 13CNMR d 32.0, 55.1, 55.3, 112.1, 114.1, 114.5, 120.5, 121.0, 124.6, 127.7, 129.6, 138.3, 150.5, 159.8, 161.1, 161.3. Anal calc d for C18H17NO3: C, 73.20; H, 5.80; N, 4.74. Found C, 73.27; H, 5.81; N, 4.74. (Table 2, entry 9) 2-Phenyl-5-(4-methoxybenzyl)oxazole; mp: oil; IR (neat): 2838, 820, 705, 699 cm-1. 1H NMR d 3.71 (s, 3H), 3.93 (s, 3H); 6.75 (s, 1H), 6.79 (d, J = 8.6 Hz, 2H), 7.12 (d, J = 8.6 Hz, 2H), 7.27-7.39 (m, 3H), 7.85-7.97 (n, 2H). 13CNMR d 31.3, 55.3, 114.1, 124.6, 126.1, 127.7, 128.7, 128.8, 129.7, 130.1, 151.9, 158.5, 161.2. Anal calc d for C17H15NO2: C, 76.96; H, 5.70; N, 5.28. Found C, 76.90; H, 5.71; N, 5.26. (Table 2, entry 10) 2-Phenyl-5-benzyloxazole; mp: oil; IR (neat): 2835, 825, 711, 695 cm-1. 1H NMR d 4.04 (s, 2H), 6.85 (s, 1H), 7.28-7.41 (m, 8H), 7.96-8.01 (m, 2H). 13CNMR d 32.2, 124.9, 126.1, 126.9, 127.7, 128.7, 130.0, 136.8, 151.4, 161.3. Anal calc d for C16H13NO: C, 81.68; H, 5.57; N, 5.95. Found C, 81.59; H, 5.55; N, 5.94. (Table 2, entry 11) 2-Phenyl-5-(4-chlorobenzyl)oxazole; mp: oil; IR (neat): 2828, 824, 709, 695 cm-1. 1H NMR d 3.96(s, 2H), 6.81(s, 1H), 6.81(s, 1H), 7.33-7.40(m, 3H), 7.89-7.96(m, 2H). 13CNMR d 31.4, 124.9, 126.0, 127.5, 128.7, 128.8, 130.0, 130.1, 132.8, 135.1, 150.7, 161.3. Anal calcd for C16H12ClNO: C, 71.25; H, 4.48; N, 5.19. Found C, 71.19; H, 4.46; N, 5.18. (Table 2, entry 12) 2-(4-Methoxyphenyl)-5-(4-chlorobenzyl)oxazole; mp: oil; IR (neat): 2836, 830 cm-1. 1H NMR d 3.78 (s, 3H), 3.95 (s, 2H), 6.77 (s, 1H), 6.87-6.92 (m, 2H), 7.13-7.28 (m, 4H), 7.86-7.90 (m, 2H). 13CNMR d 31.4, 55.3, 114.1, 120.3, 124.7, 127.7, 128.8, 130.0, 132.7, 135.7, 150.1, 161.1, 161.4. Anal calc d for C17H14ClNO2: C, 68.12; H, 4.71; N, 4.67. Found C, 68.19; H, 4.72; N, 4.68. (Table 2, entry 13) 2-(3-Trifluoromethylphenyl)-5-(4-chlorobenzyl)oxazole; mp: oil; IR (neat): 2840, 820. 1H NMR d 4.04 (s, 3H), 6.89 (s, 1H), 7.19-7.33 (m, 4H), 7.51-7.68 (m, 2H), 8.13-8.25(m, 2H). 13CNMR d 31.6, 123.0 (q, J = 3.9 Hz), 123.9 (q, J = 273.0 Hz), 123.1, 125.4, 126.6 (q, J = 3.9 Hz), 126.7, 128.3, 129.0, 129.2, 129.4, 130.1, 132.2, 133.1, 134.9, 151.7, 160.1. Anal calcd for C17H11ClF3NO: C, 60.46; H, 3.28; N, 4.15. Found C, 60.51; H, 3.29; N, 4.14. (Table 2, entry 14) 2-(4-Methylphenyl)-5-(4-chlorobenzyl)oxazole; mp: oil; IR (neat): 2835, 830 cm-1. 1H NMR d 2.39 (s, 3H), 4.02 (s, 2H), 6.83 (s, 1H), 7.19-7.33 (m, 6H), 7.84-7.89 (m, 2H). 13CNMR d 21.5, 31.3, 123.7, 127.4, 128.6, 130.0, 131.7, 134.5, 136.0, 136.1, 141.4, 150.7, 161.3. Anal calc d for C17H14ClNO: C, 71.96; H, 4.97; N, 4.94. Found C, 71.91; H, 4.98; N, 4.93. (Table 2, entry 15) 2-Phenyl-5-(3-trifluoromethylbenzyl)oxazole; mp: oil; IR (neat): 2835, 827, 712, 691 cm-1. 1H NMR d 2.12 (s, 2H), 6.90 (s, 1H), 7.41-7.56 (m, 7H), 7.96-8.01 (m, 2H). 13CNMR d 31.8, 123.9 (q, J = 272.8 Hz), 124 (q, J = 3.7 Hz), 125.1, 125.5 (q, J = 3.7 Hz), 126.1, 127.4, 128.7, 129.1, 130.2, 131.1 (q, J = 32.4 Hz), 132.0, 137.6, 150.1, 161.5. Anal calcd for C17H12F3NO: C, 67.32; H, 3.99; N, 4.62. Found C, 67.39; H, 3.97; N, 4.63. (Table 2, entry 16) 2-Phenyl-5-(3-fluorobenzyl)oxazole; mp: oil; IR (neat): 2830, 933, 712, 691 cm-1. 1H NMR d 4.04 (s, 2H), 6.88-7.06 (m, 4H), 7.22-7.29 (m, 1H), 7.22-7.29 (m, 1H), 7.39-7.45 (m, 3H), 7.96-8.01 (m, 2H). 13CNMR d 31.8 (d, J = 1.8 Hz), 113.9 (d, J = 20.3 Hz), 115.7 (d, J = 22.3 Hz), 124.3 (d, J = 3.0 Hz), 125.1, 126.0, 126.1, 127.6, 130.17, 130.2, (d, J = 8.3 Hz) 139.1 (d, J = 7.4 Hz), 150.5, 161.5, 163.0 (d, J = 246.0 Hz). Anal calcd for C16H12FNO: C, 75.88; H, 4.78; N, 5.53. Found C, 75.80; H, 4.77; N, 5.55. (Table 2, entry 17) 2-Phenyl-5-(4-fluorobenzyl)oxazole; mp: oil; IR (neat): 2830, 829, 708, 695 cm-1. 1H NMR d 4.01 (s, 2H), 6.84 (d, J = 0.5 Hz, 1H), 6.96-7.27 (m, 4H), 7.39-7.43 (m, 3H), 7.96-8.01 (m, 2H). 13CNMR d 31.5, 115.6 (d, J = 21.3 Hz), 124.9, 126.1, 127.6, 128.7, 130.1, 130.3, 132.3, (d, J = 3.1 Hz), 151.2, 161.4, 161.9 (d, J = 243.5 Hz). Anal calc d for C16H12FNO: C, 75.88; H, 4.78; N, 5.53. Found C, 75.81; H, 4.76; N, 5.50. (Table 2, entry 18) 2-Trifluoromethyl-5-(4-acetylbenzyl)oxazole; mp: oil; IR (neat): 2835, 1676, 820 cm-1. 1H NMR d 2.57 (s, 3H), 4.10 (s, 2H), 6.90 (s, 1H), 7.32 (d, J = 8.0 Hz, 2H), 7.92 (d, J = 8.0 Hz, 2H). 13CNMR d 26.6, 31.9, 116.4 (q, J = 268.7 Hz), 124.9, 129.0, 129.1, 136.4, 140.4, 150.4 (q, J = 43.7 Hz), 153.5, 197.5. Anal calc d for C13H10F3NO2: C, 58.00; H, 3.74; N, 5.20. Found C, 58.08; H, 3.72; N, 5.21. (Table 2, entry 19) 2-Phenyl-5-(4-acetylbenzyl)oxazole; mp: oil; IR (neat): 2835, 1677, 820 cm-1. 1H NMR d 2.47 (s, 3H), 4.00 (s, 2H), 6.79 (s, 1H), 7.18-7.39 (m, 5H), 7.82 (d, J = 8.1 Hz, 2H), 7.81-7.93 (m, 2H). 13CNMR d 26.6, 32.1, 125.2, 126.2, 127.4, 128.8, 128.9, 130.3, 136.0, 142.1, 150.3, 161.5, 197.6. Anal calcd for C18H15NO2: C, 77.96; H, 5.45; N, 5.05. Found C, 78.03; H, 5.44; N, 5.06. (Table 2, entry 20) 2-(3-trifluoromethylphenyl)-5-(4-acetylbenzyl)oxazole; mp: oil; IR (neat): 2835, 1691, 825 cm-1. 1H NMR (CHCl3) d 2.57 (s, 3H), 4.13 (s, 2H), 6.92 (s, 1H), 7.37 (d, J = 8.3 Hz, 2H), 7.53-7.67 (m, 2H), 7.92 (d, J = 8.3 Hz, 2H), 8.12-8.23 (m, 2H). 13CNMR d 26.7, 32.1, 115.7, 121.1, 123.0 (q, J = 272.8 Hz), 125.6, 126.5, 126.7 (q, J = 3.7 Hz), 128.3, 128.4, 129.0, 129.24, 129.26, 129.4, 130.4, 131.3 (q, J = 3.7 Hz), 131.9, 197.7. Anal calcd for C19H14F3NO2: C, 66.09; H, 4.09; N, 4.06. Found C, 66.15; H, 4.10; N, 4.08. (Table 2, entry 21) 2-(4-Methoxyphenyl)-5-(4-acetylbenzyl)oxazole; mp: oil; IR (neat): 2828, 1676, 825 cm-1. 1H NMR d 2.51 (s, 3H), 3.76 (s, 3H), 4.03 (s, 2H), 6.79-6.89 (m, 3H), 7.28-7.33 (m, 2H), 7.83-7.88 (m, 4H). 13CNMR d 26.5, 32.0, 55.3, 114.1, 120.3, 124.9, 127.7, 128.7, 128.8, 135.8, 142.3, 149.6, 161.2, 161.5, 197.5. Anal calc d for C19H17NO3: C, 74.25; H, 5.58; N, 4.56. Found C, 74.31; H, 5.59; N, 4.54. (Table 2, entry 22) 2-(4-Methylphenyl)5-(4-acetylbenzyl)oxazole; mp: oil; IR (neat): 2830, 1677, 820 cm-1. 1H NMR d 2.35 (s, 3H), 2.56 (s, 3H), 4.05 (s, 2H), 6.85 (s, 1H), 7.19-7.37 (m, 4H), 7.83-7.93 (m, 4H). 13CNMRs d 21.5, 26.6, 32.1, 124.8, 125.0, 126.1, 128.8, 128.9, 129.5, 135.9, 140.5, 142.3, 149.9, 161.7, 197.7. Anal calc d for C19H17NO2: C, 78.33; H, 5.88; N, 4.81. Found C, 78.41; H, 5.86; N, 4.83. RS@Bjn   \ ` d f r t d h r t       , . 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