M. Bergagnini-Kolev, M. Howe, E. Burgess et al.
Tetrahedron 77 (2021) 131741
133.2, 133.7, 138.8, 142.2, 153.0, 170.0, 171.0, 175.8, 176.7. HRMS
(trifluoromethyl)-benzoyl)-phenyl)-2-piperidyl-acetamide 9f:
[M þ Naþ] found m/s 689.1902, calcd for C36H38N4NaNiO5 689.1886.
M.p. >200 ꢀC (decomp.). 1H NMR
d
1.02 (3H, d, J ¼ 7.14 Hz), 1.04 (3H,
[
a
]
25 þ2320 (c 0.105, CH3Cl).
d, J ¼ 7.54 Hz), 1.26e1.82 (7H, m), 2.31 (1H, m), 2.63 (1H, m), 2.99
(1H, m), 3.12e3.47 (3H, m), 3.72 (1H, AB, J ¼ 16.4 Hz), 3.83 (2H, m),
3.97 (1H, m), 4.11 (1H, m), 4.45 (1H, t, J ¼ 8.40 Hz), 5.10 (1H, m), 6.54
(1H, d, J ¼ 8.22 Hz), 6.80 (1H, t, J ¼ 7.35 Hz), 7.16 (2H, m), 7.37 (4H,
m), 7.49 (1H, s), 7.67 (1H, s), 7.77 (1H, m), 8.65 (1H, d, J ¼ 8.67 Hz).
D
Ni(II) Complex of (2S,3S)-3-methyl-5-[(4′S)-4′-phenyl-2′-
oxazolidinonyl)]glutamic acid Schiff Base with N-(2-(4-
trifluoromethylbenzoyl)-phenyl)-2-piperidyl-acetamide 9b:
M.p. 182.4 ꢀC (decomp.). 1H NMR
1.26e1.91 (7H, m), 2.27 (3H, d,
d
J ¼ 6.03 Hz), 2.32 (1H, m), 2.71 (1H, dd, J ¼ 18.6, 4.02 Hz), 3.00e3.41
(4H, m), 3.69 (1H, AB, J ¼ 16.5 Hz), 3.81 (1H, AB, J ¼ 16.5 Hz), 3.95
(1H, d, J ¼ 4.02 Hz), 4.20 (1H, dd, J ¼ 8.80, 2.43 Hz), 4.55 (1H, t,
J ¼ 8.58 Hz), 5.12 (1H, dd, J ¼ 8.25, 2.43 Hz), 6.62 (1H, m), 6.76 (1H,
m), 7.11 (1H, m), 7.18 (2H, m), 7.28e7.38 (5H, m), 7.63 (1H, d,
13C NMR
d 16.9, 19.3, 20.0, 22.8, 23.2, 26.9, 30.6, 43.6, 54.4, 56.8,
57.6, 60.7, 70.1, 70.9, 121.6, 123.7, 125.7, 125.9, 126.1 (1C, q,
J ¼ 272.3 Hz), 126.2, 126.5 (1C, q, J ¼ 273.8 Hz), 127.5, 128.6, 129.0,
129.3, 132.6 (1C, q, J ¼ 35.2 Hz), 132.8 (1C, q, J ¼ 33.8 Hz), 133.4,
133.5, 135.6, 139.3, 143.1, 153.7, 168.1, 171.2, 176.5, 177.6. HRMS
J ¼ 8.01 Hz), 8.60 (1H, d, J ¼ 8.58 Hz). 13C NMR
d
17.3,19.4, 20.0, 22.9,
[M þ Hþ] found m/s 831.2107, calcd for C39H39F6N4NiO6 831.2122.
25
33.6, 38.7, 54.4, 57.1, 57.3, 60.8, 70.0, 73.0, 121.3, 123.7, 123.8 (1C, q,
J ¼ 271.5 Hz), 126.1, 126.3, 126.4, 127.9, 128.6, 128.8, 129.0, 129.1,
131.8 (1C, q, J ¼ 32.5 Hz),133.1,133.6, 137.1, 139.2,142.8,153.4,169.9,
170.0, 176.3, 176.7. HRMS [M þ Hþ] found m/s 735.1937, calcd for
[
a
]
D
þ1487 (c 0.45, CH3Cl).
Ni(II) Complex of (2S,3R)-3-(2-trifluoromethylphenyl)-5-[(4′
S)-4′-phenyl-2′-oxazolidinonyl)]glutamic acid Schiff Base with
N-(2-benzoylphenyl)-2-piperidyl-acetamide 9g: [12b] M.p.
C
36H36F3N4NiO6 7351935. [
a
]
25 þ1604 (c 0.85, CH3Cl).
>200 ꢀC (decomp.). 1H NMR
d 1.19e1.80 (7H, m), 2.50e2.74 (2H, m),
D
Ni(II) Complex of (2S,3S)-3-methyl-5-[(4′S)-4′-phenyl-2′-
2.99 (1H, m), 3.29 (1H, m), 3.44 (1H, d, J ¼ 16.1 Hz), 3.50e3.67 (2H,
m), 4.13 (1H, dd, J ¼ 8.79, 3.42 Hz), 4.23 (1H, m), 4.33 (1H, d,
J ¼ 4.89 Hz), 4.49 (1H, t, J ¼ 8.79 Hz), 5.16 (1H, dd, J ¼ 8.54, 3.42 Hz),
6.56 (1H, bs), 6.66e6.75 (2H, m), 6.94e7.20 (2H, m), 7.10e7.30 (6H,
m), 7.40e7.57 (5H, m), 7.72 (1H, d, J ¼ 7.62 Hz), 8.62 (1H, d,
oxazolidinonyl)]glutamic acid Schiff Base with N-(2-(3,5-bis-
(trifluoromethyl)-benzoyl)-phenyl)-2-piperidyl-acetamide 9c:
M.p. 193.8 ꢀC (decomp.). 1H NMR
d 1.33e2.10 (7H, m), 2.40 (3H, d,
J ¼ 6.93 Hz), 2.66 (1H, m), 2.96 (2H, m), 3.18 (1H, m), 3.34 (2H, m),
3.66 (2H, m), 4.08 (2H, m), 4.52 (1H, t, J ¼ 8.79 Hz), 4.88 (1H, dd,
J ¼ 8.64, 3.06 Hz) 6.42 (1H, m), 6.71 (1H, m), 7.03 (2H, m), 7.20e7.31
(5H, m), 7.61 (1H, s), 6.76 (1H, s), 8.47 (1H, d, J ¼ 8.58 Hz). 13C NMR
J ¼ 8.55 Hz). 13C NMR
d 19.5, 20.0, 22.9, 38.3, 40.7, 54.4, 55.7, 57.3,
60.4, 69.9, 74.0, 120.6122.6, 123.8 (q, J ¼ 273.7 Hz), 125.4, 126.4,
126.4, 126.4 (q, J ¼ 5.92 Hz), 127.2, 127.4, 127.9, 128.1, 128.6, 128.7,
129.0, 129.5, 129.8 (q, J ¼ 29.4 Hz), 130.2, 132.0, 132.8, 133.1, 134.1,
138.0, 138.3, 142.8, 153.3, 168.6, 172.5, 175.3, 176.3. HRMS [M þ Naþ]
d
17.1, 19.3, 20.0, 22.8, 33.2, 38.3, 54.5, 57.3, 57.5, 60.6, 69.9, 71.9,
121.5, 122.5 (1C, q, J ¼ 275.2 Hz), 123.0 (1C, q, J ¼ 275.2 Hz), 124.0,
124.8, 125.7, 126.3, 127.4, 128.3, 128.5, 128.9, 132.5 (1C, q,
J ¼ 33.4 Hz), 132.6 (1C, q, J ¼ 33.4 Hz), 133.1, 133.3, 135.4, 139.3,
found m/s 819.1591, calcd for
C42H39F3N4NaNiO5 819.1916.
25
[
a
]
D
þ1810 (c 0.106, CH3Cl).
142.9, 153.4, 167.9, 169.8, 176.2, 176.5. HRMS [M þ Hþ] found m/s
Ni(II) Complex of (2S,3R)-3-(2-trifluoromethylphenyl)-5-[(4′
25
803.1816, calcd for C37H35F6N4NiO6 803.1809. [
CH3Cl).
a
]
þ1467 (c 1.29,
S)-4′-phenyl-2′-oxazolidinonyl)]glutamic acid Schiff Base with
N-(2-(4-trifluoromethylbenzoyl)-phenyl)-2-piperidyl-acet-
D
Ni(II) Complex of (2S,3R)-3-isopropyl-5-[(4′S)-4′-phenyl-2′-
oxazolidinonyl)]glutamic acid Schiff Base with N-(2-
benzoylphenyl)-2-piperidyl-acetamide 9d: [12b] M.p. >190 ꢀC
amide 9h: M.p. >200 ꢀC (decomp.). 1H NMR
d 1.26e1.75 (7H, m),
2.40 (1H, m), 2.56 (1H, m), 2.92 (1H, m), 3.24e3.38 (3H, m), 3.94
(2H, m), 4.17 (1H, dd, J ¼ 8.76, 2.76 Hz), 4.27 (1H, m), 4.57 (1H, t,
J ¼ 8.61 Hz), 5.08 (1H, dd, J ¼ 8.37, 2.65 Hz), 6.61 (1H, m), 6.73 (1H,
m), 7.04 (2H, m), 7.26e7.31 (5H, m), 7.35 (1H, m), 7.53 (1H, m), 7.61
(1H, m), 7.76 (3H, m), 7.84 (1H, m), 8.58 (1H, d, J ¼ 8.58 Hz). 13C NMR
(decomp.). 1H NMR
d
0.25 (3H, d, J ¼ 6.84 Hz), 0.88 (3H, d,
J ¼ 6.84 Hz), 1.20e1.84 (7H, m), 2.34 (1H, m), 2.51 (1H, dd, J ¼ 19.0,
1.47 Hz) 2.92 (1H, m), 3.10 (1H, dd, J ¼ 19.0, 10.0 Hz), 3.14 (1H, m),
3.26e3.45 (2H, m), 3.61 (1H, m), 3.64e3.76 (2H, m), 3.90e4.03 (2H,
m), 5.32 (1H, dd, J ¼ 6.14, 3.35 Hz), 6.79 (1H, ddd, J ¼ 8.30, 6.96,
1.22 Hz), 6.87 (1H, dd, J ¼ 8.30, 1.71 Hz), 7.12e7.59 (11H, m), 8.73
d
19.5, 19.9, 22.8, 38.1, 40.1, 54.7, 55.8, 57.2, 60.4, 70.1, 73.3, 120.9,
122.8, 123.7 (1C, q, J ¼ 273.2 Hz), 124.9 (1C, q, J ¼ 271.6 Hz), 125.6,
125.9, 126.2, 126.9, 127.9, 128.0, 128.4, 128.7, 128.9, 130.0 (1C, q,
J ¼ 30.9 Hz),131.2,131.7 (1C, q, J ¼ 33.2 Hz),131.9,132.6,133.3,133.8,
136.9, 138.6, 138.7, 143.1, 153.5, 168.8, 171.4, 175.1, 176.6. HRMS
(1H, dd, J ¼ 8.66, 1.22 Hz. 13C NMR
d 15.6, 19.1, 19.8, 21.6, 22.9, 27.4,
31.5, 45.3, 53.7, 56.1, 57.2, 60.6, 70.5, 72.1, 121.1, 122.7, 125.3, 125.7,
127.8, 128.4, 128.8, 128.9, 129.1, 129.1, 129.7, 132.6, 133.3, 134.3,
[M þ Hþ] found m/s 865.1979, calcd for C42H37F6N4NiO6 865.1965.
25
139.0, 142.4, 153.5, 171.1, 172.3, 176.5, 178.0. HRMS [M þ Naþ] found
[
a
]
D
þ1143 (c 0.96, CH3Cl).
25
m/s 717.2361, calcd for C38H42N4NaNiO6 717.2199. [
a
]
þ2187 (c
Ni(II) Complex of (2S,3R)-3-(2-trifluoromethylphenyl)-5-[(4′
D
0.104, CH3Cl).
S)-4′-phenyl-2′-oxazolidinonyl)]glutamic acid Schiff Base with
N-(2-(3,5-bis-(trifluoromethyl)-benzoyl)-phenyl)-2-piperidyl-
Ni(II) Complex of (2S,3R)-3-isopropyl-5-[(4′S)-4′-phenyl-2′-
oxazolidinonyl)]glutamic acid Schiff Base with N-(2-(4-
acetamide 9i: M.p. >167.5 ꢀC. 1H NMR
d 1.20e1.68 (7H, m), 2.17 (1H,
trifluoromethylbenzoyl)-phenyl)-2-piperidyl-acetamide
9e:
0.46 (3H, d, J ¼ 6.69 Hz), 0.92
m), 2.52 (2H, m), 2.93 (2H, m), 3.25 (2H, m), 3.53 (1H, m), 4.13 (1H,
m), 4.16 (1H, dd, J ¼ 8.79, 3.15 Hz), 4.41 (1H, d, J ¼ 4.05 Hz), 4.63 (1H,
t, J ¼ 8.76 Hz), 4.97 (1H, dd, J ¼ 8.58, 2.97 Hz), 6.51 (1H, m), 6.75 (1H,
m), 7.05 (2H, m), 7.26e7.43 (6H, m), 7.71 (1H, s), 7.82 (1H, s), 7.99
M.p. >190 ꢀC (decomp.). 1H NMR
d
(3H, d, J ¼ 6.81 Hz), 1.36e1.79 (7H, m), 2.51 (1H, m), 2.80 (1H, m),
2.93 (1H, m), 3.16 (2H, m), 3.28e3.40 (2H, m), 3.58 (1H, m), 3.71
(1H, m), 3.94 (1H, m), 4.04 (1H, dd, J ¼ 8.55, 1.98 Hz), 4.12 (1H, t,
J ¼ 8.45 Hz), 5.29 (1H, dd, J ¼ 6.21, 3.25 Hz), 6.73 (1H, m), 6.81 (1H,
m), 7.27 (2H, m), 7.31e7.43 (6H, m), 7.79 (2H, d, J ¼ 8.22 Hz), 8.73
(2H, m), 8.49 (1H, d, J ¼ 8.61 Hz). 13C NMR
d 19.6, 19.9, 22.8, 38.4,
39.1, 54.8, 56.0, 57.6, 60.4, 70.1, 72.2, 121.1, 123.2, 125.4, 126.1 (1C, q,
J ¼ 271.6), 126.3, 126.7 (1C, q, J ¼ 273.1 Hz), 126.8, 126.9, 127.3, 127.9
(1C, q, J ¼ 271.6), 128.1, 128.6, 128.9, 129.0 (1C, q, J ¼ 30.1 Hz), 129.9
(1C, q, J ¼ 30.1 Hz), 130.1, 131.9, 132.4 (1C, q, J ¼ 33.7 Hz), 132.9,
133.3, 133.6, 135.3, 138.5, 138.8, 143.3, 153.5, 169.1, 169.2, 174.7,
(1H, d, J ¼ 8.61 Hz). 13C NMR
d 16.0, 19.2, 19.9, 22.1, 22.9, 27.4, 31.3,
45.1, 54.1, 56.5, 57.4, 60.8, 70.5, 72.2, 121.6, 123.3, 123.5 (1C, q,
J ¼ 270.8 Hz), 125.7, 125.8, 126.4, 126.5, 128.6, 128.7, 129.2, 129.6,
132.1 (1C, q, J ¼ 30.3 Hz), 133.3, 134.1, 137.3, 139.2, 142.9, 153.9,
170.0, 172.2, 176.9, 177.9. HRMS [M þ Hþ] found m/s 763.2255, calcd
177.0. HRMS [M
þ
Hþ] found m/s 933.1852, calcd for
C
43H36F9N4NiO6 933.1839. [
a
]
25 þ962 (c 1.12, CH3Cl).
D
for C38H40F3N4NiO6 763.2248. [
Ni(II) Complex of (2S,3R)-3-isopropyl-5-[(4′S)-4′-phenyl-2′-
oxazolidinonyl)]glutamic acid Schiff Base with N-(2-(3,5-bis-
a
]
25 þ1610 (c 0.65, CH3Cl).
Ni(II) Complex of (2S,3R)-3-(2-methoxyphenyl)-5-[(4′S)-4′-
D
phenyl-2′-oxazolidinonyl)]glutamic acid Schiff Base with N-(2-
benzoylphenyl)-2-piperidyl-acetamide 9j: [12b] M.p. >190 ꢀC
8