Page 29 of 44
The Journal of Organic Chemistry
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1122, 1013, 992, 818, 808, 580 cm-1; H NMR (400 MHz, CDCl3) δ 2.95 (s, 6H), 2.98
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(s, 6H), 6.62−6.66 (m, 2H), 6.71−6.75 (m, 2H), 7.01−7.06 (m, 2H), 7.16−7.20 (m, 2H),
9.79 (s, 1H); 13C NMR (100 MHz, CDCl3) δ 40.3, 40.4, 112.2, 112.3, 123.7, 127.6,
130.6, 136.1, 149.3, 149.5, 188.0; MS (EI) m/z 299 (M+); HRMS (EI) Calcd for
C17H21N3S : 299.1456; found : 299.1447.
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(4R*,5S*)-4,5-Dihydro-2-(4-pyridyl)-N,N,4-triphenyl-5-thiazolamine
(7).
According to the general procedure for thiazolines, compound 7 was prepared. The
crude material was purified by column chromatography (SiO2, hexane:EtOAc:Et3N =
5:1:0.01) to give 7 (0.65 g, 80%) as an orange solid (mp 52−55 ℃): IR (KBr) 3054,
3026, 3005, 1591, 1548, 1491, 1448, 1410, 1266, 1236, 1213, 1032, 1002, 992, 963,
831, 753, 728, 694 cm-1; 1H NMR (400 MHz, CDCl3) δ 5.97 (d, J = 3.4 Hz, 1H), 6.32 (d,
J = 3.4 Hz, 1H), 6.96 (d, J = 7.8 Hz, 4H), 7.00−7.05 (m, 2H), 7.18−7.29 (m, 9H), 7.58
(d, J = 5.9 Hz, 2H), 8.62 (d, J = 5.9 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ 82.1, 82.6,
119.8, 121.6, 121.9, 123.4, 124.0, 126.2, 127.4, 128.1, 128.8, 129.3, 129.4, 139.2, 140.4,
145.4, 150.3, 166.8; MS (EI) m/z 407 (M+); HRMS (EI) Calcd for C26H21N3S :
407.1456; found : 407.1449.
(4R*,5S*)-2-[1,1’-Biphenyl]-4-yl-4,5-dihydro-N,N,4-triphenyl-5-thiazolamine (8).
According to the general procedure for thiazolines, compound 8 was prepared. The
crude material was purified by column chromatography (SiO2, hexane:EtOAc = 15:1) to
give 8 (0.87 g, 60%) as a brown liquid: IR (KBr) 3059, 3029, 2956, 2926, 1686, 1597,
1491, 1450, 1276, 1241, 1034, 948, 908, 846, 751, 728, 696 cm-1; 1H NMR (400 MHz,
CDCl3) δ 6.03 (d, J = 3.9 Hz, 1H), 6.32 (d, J = 3.9 Hz, 1H), 7.04−7.07 (m, 5H),
7.28−7.41 (m, 12H), 7.44−7.48 (m, 2H), 7.61−7.66 (m, 4H), 7.96 (d, J = 6.8 Hz, 1H);
13C NMR (100 MHz, CDCl3) δ 81.5, 82.4, 117.7, 121.4, 123.4, 123.8, 125.0, 126.1,
126.3, 127.1, 127.9, 128.8, 128.9, 129.4, 129.6, 140.0, 144.0, 145.6, 161.7; MS (EI) m/z
482 (M+); HRMS (EI) Calcd for C33H26N2S : 482.1817; found : 482.1811.
(4R*,5S*)-4,5-Dihydro-4-(2-methylphenyl)-N,N,2-triphenyl-5-thiazolamine
(9).
According to the general procedure for thiazolines, compound 9 was prepared. The
crude material was purified by column chromatography (SiO2, hexane:EtOAc:Et3N =
45:1:0.01) to give 9 (0.21 g, 50%) as a brown solid (mp 128−137 ℃): IR (KBr) 2923,
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1596, 1587, 1490, 1034, 949, 766, 754, 704, 689 cm-1; H NMR (400 MHz, CDCl3) δ
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