10.1002/ejoc.202100412
European Journal of Organic Chemistry
COMMUNICATION
(400 MHz, DMSO-d6): δ = 4.07 (q, J = 7.0 Hz, 2H, OCH2), 1421, 1396, 1374, 1352, 1193 (vs), 1163 (s), 1139, 1096,
3.05 (s, 6H, N(CH3)2), 2.85 (t, J = 6.8 Hz, 2H, CH2), 2.68 (t, 1019, 997, 935, 860, 791, 699, 582, 569, 511 cm–1. MS, m/z
J = 6.8 Hz, 2H, CH2), 1.17 (t, J = 7.0 Hz, 3H, CH3) ppm. 13
C
(Irel, %): 296.2 [M+H]+ (100). Found, %: C 52.99; H 5.82; N
NMR (DMSO-d6): δ = (126 MHz, DMSO) δ 171.4 (C=O), 14.18. C13H17N3O5. Calculated, %: C, 52.88; H, 5.80; N,
160.9 (C-5 oxazole), 152.1 (C-2 oxazole), 116.7 (CN), 14.23.
82.4 (C-4 oxazole), 60.1 (OCH2), 38.2 2 (N(CH3)2), 29.7
Ethyl 3-(4-cyano-5-(phenylamino)oxazol-2-yl)propanoate
(CH2), 22.3 (CH2), 14.0 (CH3) ppm. IR (KBr): ṽ = 3007,
(11ce). Yield 767 mg (67 %), brown solid, mp 118–120 °C;
2988, 2966, 2939, 2807, 2201 (vs), 1730 (s), 1655 (vs, br),
1605, 1462, 1430, 1414, 1393, 1371, 1352, 1300, 1271,
1225, 1199, 1171, 1148, 1108, 1093, 1053, 1015, 994, 968,
Rf = 0.35 (CH2Cl2–MeOH, 95:5). 1H NMR (400 MHz,
DMSO-d6): δ = 10.24 (s, 1H, NH), 7.34 (t, J = 7.9 Hz, 2H,
H-3,5 Ph), 7.21 (d, J = 7.7 Hz, 2H, H-2,6 Ph), 7.05 (t, J =
7.4 Hz, 1H, H-4 Ph), 4.08 (q, J = 7.4 Hz, 2H, OCH2), 2.95 (t,
936, 880, 857, 792, 744, 690, 663, 639, 621, 594, 511, 489
cm–1. MS, m/z (Irel, %): 238.2 [M+H]+ (100). Found, %: C
J = 7.0 Hz, 2H, CH2), 2.73 (t, J = 7.1 Hz, 2H, CH2), 1.17 (t,
55.80; H 6.33; N 17.69. C11H15N3O3. Calculated, %: C,
55.69; H, 6.37; N, 17.71.
J = 7.1 Hz, 3H, CH3) ppm. 13C NMR (126 MHz, DMSO-d6):
δ = 171.5 (C=O), 156.8 (C-5 oxazole), 154.4 (C-2 oxazole),
Ethyl 3-(4-cyano-5-morpholinooxazol-2-yl)propanoate 138.8, 129.4 2 (Ph), 123.1, 118.4 2 (Ph), 114.6 (CN),
(11cb). Yield 1032 mg (92 %), colorless solid, mp 41– 88.1 (C-4 oxazole), 60.3 (OCH2), 30.0 (CH2), 22.7 (CH2),
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43 °C; Rf = 0.3 (CH2Cl2–MeOH, 95:5). H NMR (400 MHz, 14.2 (CH3) ppm. IR (KBr): ṽ = 3329, 3280, 3226, 3152,
DMSO-d6): δ = 4.07 (q, J = 7.1 Hz, 2H, OCH2), 3.74 – 3.67 3109, 3077, 3017, 2982, 2934, 2224 (s), 1726 (s), 1677 (vs),
(m, 4H, O(CH2)2), 3.46 – 3.39 (m, 4H, N(CH2)2), 2.87 (t, J = 1604, 1588, 1516, 1502, 1440, 1423, 1400, 1387, 1325,
6.9 Hz, 2H, CH2), 2.70 (t, J = 7.0 Hz, 2H, CH2), 1.17 (t, J = 1256, 1221, 1193, 1156, 1117, 1067, 1018, 955, 932, 894,
7.1 Hz, 3H, CH3) ppm. 13C NMR (126 MHz, DMSO-d6): δ 884, 876, 864, 798, 753, 688, 652, 495 cm–1. MS, m/z (Irel,
= 171.4 (C=O), 160.4 (C-5 oxazole), 153.2 (C-2 oxazole), %): 286.0 [M+H]+ (100). Found, %: C 63.27; H 5.24; N
115.9 (CN), 84.5 (C-4 oxazole), 65.0 2 (2 OCH2), 60.2 14.77. C15H15N3O3. Calculated, %: C, 63.15; H, 5.30; N,
(OCH2), 46.0 2 (2 NCH2), 29.7 (CH2), 22.4 (CH2), 14.0 14.73.
(CH3) ppm. IR (KBr): ṽ = 2989, 2925, 2870, 2208 (s), 1722
(vs), 1636 (vs), 1589 (vs), 1454, 1427, 1404, 1375, 1337,
1277 (s), 1233, 1206, 1187, 1157, 1117 (s), 1068, 1045,
2-Benzyl-5-(dimethylamino)oxazole-4-carbonitrile (11da).
Yield 770 mg (85 %), yellow solid, mp 43–45 °C; Rf = 0.7
(CH2Cl2–MeOH, 95:5). 1H NMR (500 MHz, DMSO-d6): δ =
1022, 966, 921, 870, 851, 804, 780, 695, 658, 570, 537, 516
7.33 (t, J = 7.4 Hz, 2H, Ph), 7.30 – 7.23 (m, 3H, Ph), 3.98 (s,
cm–1. MS, m/z (Irel, %): 280.0 [M+H]+ (100). Found, %: C
2H, CH2), 3.02 (s, 6H, N(CH3)2). ppm. 13C NMR (125 MHz,
56.03; H 6.18; N 15.05. C13H17N3O4. Calculated, %: C,
55.91; H, 6.14; N, 15.05.
DMSO-d6): δ = 161.5 (C-5 oxazole), 152.1 (C-2 oxazole),
135.5, 129.1 2 (Ph), 129.0 2 (Ph), 127.4, 117.1 (CN),
Ethyl
3-(4-cyano-5-((2-hydroxyethyl)amino)oxazol-2- 83.1 (C-4 oxazole), 38.7 2 (N(CH3)2), 33.6 (CH2) ppm. IR
yl)propanoate (11cc). Yield 786 mg (78 %), colorless solid, (KBr): ṽ = 3083, 3065, 3035, 3009, 2919 (br), 2811, 2206
mp 39–41 °C; Rf = 0.15 (CH2Cl2–MeOH, 95:5). H NMR (s), 1655 (vs), 1599 (s), 1495, 1451, 1443, 1413, 1279, 1236,
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(400 MHz, DMSO-d6): δ = 8.08 (t, J = 5.6 Hz, 1H, NH), 1175, 1144 (s), 1109, 1066, 1029, 960, 933, 903, 848, 794,
4.83 (t, J = 5.2 Hz, 1H, OH), 4.07 (q, J = 7.0 Hz, 2H, OCH2), 736 (vs), 705 (s), 691 (s), 647, 597, 571, 512 cm–1. MS, m/z
3.55 – 3.48 (m, 2H), 3.30 – 3.24 (m, 2H, partially in water), (Irel, %): 228.0 [M+H]+ (100). Found, %: C 68.38; H 5.65; N
2.82 (t, J = 6.8 Hz, 2H), 2.67 (t, J = 6.8 Hz, 2H), 1.17 (t, J = 18.60. C13H13N3O. Calculated, %: C, 68.70; H, 5.77; N,
7.0 Hz, 3H, CH3) ppm. 13C NMR (126 MHz, DMSO-d6): δ 18.49.
= 171.4 (C=O), 161.2 (C-5 oxazole), 151.7 (C-2 oxazole),
2-Benzyl-5-morpholinooxazole-4-carbonitrile
(11db).
116.1 (CN), 81.2 (C-4 oxazole), 60.1 (OCH2), 59.5 (OCH2),
45.3 (NCH2), 29.8 (CH2), 22.3 (CH2), 14.0 (CH3) ppm. IR
(KBr): ṽ = 3401 (br), 3215, 3136, 3093, 2980, 2948, 2936,
2881, 2222 (s), 1735 (s), 1669 (vs), 1605, 1503, 1472, 1452,
1430, 1403, 1378, 1345, 1317, 1221, 1200, 1183, 1157,
1132, 1088, 1071, 1061, 1050, 1044, 1020, 964, 940, 872,
866, 789, 696, 636, 599, 507, 481 cm–1. MS, m/z (Irel, %):
254.2 [M+H]+ (100). Found, %: C 52.31; H 5.92; N 16.61.
C11H15N3O4. Calculated, %: C, 52.17; H, 5.97; N, 16.59.
Yield 874 mg (81 %), white solid, mp 92–94 °C; Rf = 0.3
(CH2Cl2–MeOH, 95:5). H NMR (400 MHz, CDCl3): δ =
1
7.37 – 7.28 (m, 2H, Ph), 7.28 – 7.20 (m, 3H, Ph), 3.92 (s,
2H, PhCH2), 3.78 – 3.70 (m, 4H, O(CH2)2), 3.50 – 3.41 (m,
4H, O(CH2)2) ppm. 13C NMR (101 MHz, CDCl3) δ = 160.77
(C-5 oxazole), 153.0 (C-2 oxazole), 134.4, 128.9 2 (Ph),
128.7 2 (Ph), 127.4, 115.6 (CN), 86.4 (C-4 oxazole),
65.7 2 (2 OCH2), 46.4 2 (2 NCH2), 34.3 (CH2) ppm. IR
(KBr): ṽ = 3066, 3032, 2979, 2931, 2908, 2873, 2851, 2205
Ethyl 3-(4-cyano-5-((2-ethoxy-2-oxoethyl)amino)oxazol- (vs), 1635 (vs), 1580, 1493, 1448, 1431, 1371, 1278, 1205,
2-yl)propanoate (11cd). Yield 712 mg (60 %), orange oil; 1192, 1112 (vs), 1069, 1043, 1025, 920, 849, 735, 707, 695,
Rf = 0.2 (CH2Cl2–MeOH, 95:5). 1H NMR (500 MHz, 657, 627, 580 cm–1. MS, m/z (Irel, %): 270.2 [M+H]+ (100).
DMSO-d6): δ = 8.50 (t, J = 6.4 Hz, 1H), 4.14 (q, J = 7.1 Hz, Found, %: C 66.77; H 5.69; N 15.54. C15H15N3O2.
2H), 4.09 – 4.03 (m, 4H), 2.84 (t, J = 6.9 Hz, 2H), 2.67 (t, J Calculated, %: C, 66.90; H, 5.61; N, 15.60.
= 6.9 Hz, 2H), 1.23 – 1.14 (m, 6H) ppm. 13C NMR (151
2-Benzyl-5-((2-hydroxyethyl)amino)oxazole-4-carbo-
MHz, DMSO-d6): δ = 171.6 (C=O), 169.4 (C=O), 161.4 (C-
nitrile (11dc). Yield 573 mg (59 %), light-brown solid, mp
5 oxazole), 152.6 (C-2 oxazole), 115.5 (CN), 82.8 (C-4
oxazole), 61.0 (OCH2), 60.3 (OCH2), 44.0 (NCH2), 29.9
(CH2), 22.6 (CH2), 14.2 (CH3), 14.1 (CH3) ppm. IR (KBr): ṽ
= 2984, 2938, 2909, 2214, 1731 (s), 1643 (vs), 1600, 1442,
66–68 °C; Rf = 0.15 (CH2Cl2–MeOH, 95:5). 1H NMR
(500 MHz, DMSO-d6): δ = 8.12 (t, J = 5.7 Hz, 1H, NH),
7.34 (t, J = 7.4 Hz, 2H, Ph), 7.29 – 7.23 (m, 3H, Ph), 4.82 (t,
J = 5.4 Hz, 1H, OH), 3.96 (s, 2H, PhCH2), 3.50 (q, J = 5.6
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