ACCEPTED MANUSCRIPT
8
Tetrahedron
1
3
Hz, 2 H), 7.57 (d, J = 7.5 Hz, 2 H). C NMR (100 MHz,
Hz, 2 H), 7.38 (d, J = 8.8 Hz, 2 H), 7.49 (d, J = 8.5 Hz, 2
1
3
CDCl ): δ = 159.7, 144.2, 137.8, 132.4, 128.7, 126.6, 92.5,
3.9, 13.3. HRMS (ESI) [M + H] Calcd for C H ON
H). C NMR (100 MHz, CDCl ): δ = 163.0, 143.8, 132.9,
3
3
+
1
131.9, 128.8, 127.8, 126.1, 30.0, 20.5, 13.9, 13.3. HRMS
11
12
+
=
2
174.0913, Found = 174.0911.
(ESI) [M + H] Calcd for C H ONCl = 236.0837,
13
15
,4-Dimethyl-5-(4′-chlorophenyl)oxazole 2p-B
Oil. IR (neat): 2360, 1712, 1491, 1264, 1090, 1009, 824,
Found = 236.0833.
2-Isopropyl-5-phenyloxazole 2a-D
Oil. IR (neat): 2974, 1697, 1554, 1288, 1138, 940, 761, 689
-
1 1
7
2
2
1
55 cm . H NMR (400 MHz, CDCl ): δ = 2.36 (s, 3 H),
3
-
1 1
.47 (s, 3 H), 7.39 (d, J = 8.4 Hz, 2 H), 7.50 (d, J = 8.7 Hz,
H). C NMR (100 MHz, CDCl ): δ = 159.5, 144.1, 132.9,
31.9, 128.8, 127.6, 126.1, 13.8, 13.1. HRMS (ESI) [M +
H] Calcd for C H ONCl = 208.0524, Found =
cm . H NMR (400 MHz, CDCl ): δ = 1.41 (d, J = 6.9 Hz,
3
13
6 H), 3.15 (sep, J = 6.9 Hz, 1 H), 7.21 (s, 1 H), 7.30 (t, J =
3
7.4 Hz, 1 H), 7.40 (t, J = 7.8 Hz, 2 H), 7.62 (d, J = 7.2 Hz,
+
13
2 H). C NMR (100 MHz, CDCl ): δ = 168.6, 150.6, 128.8,
1
1
11
3
2
08.0521.
128.3, 128.0, 123.9, 121.5, 28.5, 20.4. HRMS (ESI) [M +
+
2
-Propyl-5-phenyloxazole 2a-C
H] Calcd for C H ON = 188.1070, Found =
12
14
-
1
Oil. IR (neat): 2964, 1556, 1149, 1133, 941, 759, 690 cm .
H NMR (400 MHz, CDCl ): δ = 1.04 (t, J = 7.4 Hz, 3 H),
188.1066.
1
2-Isopropyl-5-(4’-chlorophenyl)oxazole 2c-D
3
1
.85 (sext, J = 7.4 Hz, 2 H), 2.81 (t, J = 7.4 Hz, 2 H), 7.22
Oil. IR (neat): 2974, 1567, 1485, 1407, 1139, 1092, 961,
-
1 1
(
s, 1 H), 7.30 (t, J = 7.4 Hz, 1 H), 7.40 (t, J = 7.4 Hz, 2 H),
819, 739 cm . H NMR (400 MHz, CDCl ): δ = 1.40 (d, J
3
13
7
1
1
1
.61 (d, J = 7.2 Hz, 2 H). C NMR (100 MHz, CDCl ): δ =
= 7.0 Hz, 6 H), 3.15 (sep, J = 7.0 Hz, 1 H), 7.21 (s, 1 H),
3
13
64.5, 150.8, 128.8, 128.2, 128.0, 123.9, 121.7, 30.1, 20.5,
7.37 (d, J = 8.8 Hz, 2 H), 7.55 (d, J = 8.7 Hz, 2 H).
C
+
3.7. HRMS (ESI) [M + H] Calcd for C H ON =
NMR (100 MHz, CDCl ): δ = 168.8, 149.7, 133.7, 129.0,
12
14
3
+
88.1070, Found = 188.1066.
-Propyl-5-(4’-chlorophenyl)oxazole 2c-C
126.8, 125.2, 122.0, 28.5, 20.4. HRMS (ESI) [M + H]
Calcd for C H ONCl = 222.0680, Found =
2
12
13
Oil. IR (neat): 2964, 1569, 1485, 1186, 1092, 941, 819, 737
cm . H NMR (400 MHz, CDCl ): δ = 1.04 (t, J = 7.4 Hz, 3
222.0678.
-
1 1
2-Isopropyl-5-(4’-bromophenyl)oxazole 2d-D
3
H), 1.85 (sext, J = 7.4 Hz, 2 H), 2.80 (t, J = 7.4 Hz, 2 H),
Oil. IR (neat): 2974, 1696, 1550, 1480, 1106, 1072, 940,
-
1 1
7
2
1
.21 (s, 1 H), 7.37 (d, J = 8.8 Hz, 2 H), 7.54 (d, J = 8.7 Hz,
817 cm . H NMR (400 MHz, CDCl ): δ = 1.40 (d, J = 7.0
3
13
H). C NMR (100 MHz, CDCl ): δ = 164.7, 149.8, 133.7,
Hz, 6 H), 3.14 (sep, J = 7.0 Hz, 1 H), 7.22 (s, 1 H), 7.48 (d,
3
1
3
29.0, 126.7, 125.1, 122.1, 30.1, 20.5, 13.7. HRMS (ESI)
J = 8.5 Hz, 2 H), 7.53 (d, J = 8.7 Hz, 2 H). C NMR (100
+
[M + H] Calcd for C H ONCl = 222.0680, Found =
2
MHz, CDCl ): δ = 168.9, 149.7, 132.0, 127.2, 125.4, 122.1,
12
13
3
+
22.0677.
121.8, 28.5, 20.4. HRMS (ESI) [M + H] Calcd for
2
-Propyl-5-(4’bromophenyl)oxazole 2d-C
C H ONBr = 266.0175, Found = 266.0169.
12
13
Oil. IR (neat): 2959, 1566, 1481, 1286, 1007, 940, 813, 753
2-Isopropyl-5-(4’-nitrophenyl)oxazole 2i-D
-
1 1
cm . H NMR (400 MHz, CDCl ): δ = 1.03 (t, J = 7.5 Hz, 3
Mp 75-76 °C. IR (neat): 1607, 1546, 1509, 1328, 1106, 852,
3
-
1 1
H), 1.85 (sext, J = 7.5 Hz, 2 H), 2.80 (t, J = 7.4 Hz, 2 H),
737, 687 cm . H NMR (400 MHz, CDCl ): δ = 1.43 (d, J
3
7
2
1
.23 (s, 1 H), 7.48 (d, J = 8.6 Hz, 2 H), 7.53 (d, J = 8.6 Hz,
= 6.9 Hz, 6 H), 3.19 (sep, J = 7.0 Hz, 1 H), 7.43 (s, 1 H),
13
13
H). C NMR (100 MHz, CDCl ): δ = 164.8, 149.9, 132.0,
7.76 (d, J = 9.0 Hz, 2 H), 8.28 (d, J = 8.8 Hz, 2 H).
C
3
27.2, 125.4, 122.2, 121.8, 30.1, 20.5, 13.7. HRMS (ESI)
NMR (100 MHz, CDCl ): δ = 170.5, 148.7, 146.9, 134.0,
3
+
+
[
M + H] Calcd for C H ONBr = 266.0175, Found =
125.2, 124.4, 124.2, 28.6, 20.4. HRMS (ESI) [M + H]
12
13
2
66.0169.
Calcd for C H O N = 233.0921, Found = 233.0916.
12
13
3
2
2
-Propyl-5-(4’-nitrophenyl)oxazole 2i-C
2-Isopropyl-4-methyl-5-phenyloxazole 2n-D
-
1
Mp 76-77 °C. IR (neat): 1607, 1506, 1328, 1104, 940, 851,
6
Oil. IR (neat): 2973, 1564, 1445, 1243, 1015, 764, 692 cm .
H NMR (400 MHz, CDCl ): δ = 1.39 (d, J = 6.8 Hz, 6 H),
-
1
1
1
87 cm . H NMR (400 MHz, CDCl ): δ = 1.05 (t, J = 7.5
3
3
Hz, 3 H), 1.88 (sext, J = 7.2 Hz, 2 H), 2.85 (t, J = 7.5 Hz, 2
H), 7.44 (s, 1 H), 7.76 (d, J = 9.1 Hz, 2 H), 8.28 (d, J = 9.0
2.40 (s, 3 H), 3.10 (sep, J = 7.0 Hz, 1H), 7.28 (t, J = 7.2 Hz,
1 H), 7.42 (t, J = 7.9 Hz, 2 H), 7.58 (d, J = 7.3 Hz, 2 H).
13
13
Hz, 2 H). C NMR (100 MHz, CDCl ): δ = 166.4, 148.8,
C NMR (100 MHz, CDCl ): δ = 166.9, 144.6, 131.3,
3
3
1
46.9, 134.0, 125.3. 124.4, 124.2, 30.2, 20.4, 13.7. HRMS
129.4, 128.6, 127.2, 125.1, 28.3, 20.5, 13.3. HRMS (ESI)
+
+
(
ESI) [M + H] Calcd for C H O N = 233.0921,
[M + H] Calcd for C H ON = 202.1226, Found =
12
13
3
2
13 16
Found = 233.0916.
202.1224.
2
-Propyl-4-methyl-5-phenyloxazole 2n-C
2-Isopropyl-4-methyl-5-(4’-chlorophenyl)oxazole 2p-D
Oil. IR (neat): 2974, 1569, 1490, 1388, 1245, 1010, 827,
Oil. IR (neat): 2964, 1704, 1566, 1386, 1241, 1015, 762,
5
-
1
1
-1 1
36 cm . H NMR (400 MHz, CDCl ): δ = 1.03 (t, J = 7.4
705 cm . H NMR (400 MHz, CDCl ): δ = 1.38 (d, J = 7.0
3
3
Hz, 3 H), 1.84 (sext, J = 7.6 Hz, 2 H), 2.40 (s, 3H), 2.76 (t,
J = 7.6 Hz, 2 H), 7.29 (t, J = 7.4 Hz, 1 H), 7.42 (t, J = 7.9
Hz, 2 H), 7.58 (d, J = 7.4 Hz, 2 H). C NMR (100 MHz,
Hz, 6 H), 2.38 (s, 3 H), 3.10 (sep, J = 6.8 Hz, 1 H), 7.39 (d,
J = 8.9 Hz, 2 H), 7.50 (d, J = 8.8 Hz, 2 H). C NMR (100
1
3
13
MHz, CDCl ): δ = 167.1, 143.7, 132.9, 131.8, 128.9, 127.9,
3
+
CDCl ): δ = 162.8, 144.8, 131.4, 129.4, 128.7, 127.2, 125.0,
126.2, 28.3, 20.5, 13.3. HRMS (ESI) [M + H] Calcd
3
+
3
0.1, 20.6, 13.7, 13.3. HRMS (ESI) [M + H] Calcd for
for C H ONCl = 236.0837, Found = 236.0832.
13
15
C H ON = 202.1226, Found = 202.1223.
2,5-Diphenyloxazole 2a-E
1
3
16
2
-Propyl-4-methyl-5-(4’-chlorophenyl)oxazole 2p-C
Mp 66-69 °C. IR (neat): 2359, 1542, 1480, 1133, 1058, 760,
-
1
-1 1
Oil. IR (neat): 2965, 1620, 1572, 1491, 1241, 827, 713 cm .
H NMR (400 MHz, CDCl ): δ = 1.02 (t, J = 7.4 Hz, 3 H),
705 cm . H NMR (400 MHz, CDCl ): δ = 7.35 (t, J = 7.4
3
1
Hz, 1 H), 7.43-7.52 (m, 6 H), 7.73 (d, J = 7.4 Hz, 2 H),
3
1
3
1
.83 (sext, J = 7.4 Hz, 2 H), 2.37 (s, 3 H), 2.75 (t, J = 7.6
8.12 (m, 2 H). C NMR (100 MHz, CDCl ): δ = 161.1,
3