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Organic & Biomolecular Chemistry
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NMR (100 MHz, DMSO-d6) δ 192.1, 191.7, 179.3, 155.1, 148.8, (E)-2-Amino-3-(4-(tert-butyl)benzoyl)-4-((2-(4-(tert
ARTICLE
DOI: 10.1039/C5OB02(625g9H):
146.5, 138.3, 136.1, 132.7, 132.2, 131.6, 129.6, 129.0, 128.7, butyl)benzoyl)phenyl)imino)cyclohexa-2,5-dien-1-one
128.2, 128.1, 127.9, 127.4, 127.1, 125.7, 123.9, 102.5; IR (neat) Dark red colour soild; mp 120-122oC, Rf 0.52; (hexanes : ethyl
1
3392, 3061, 2925, 1654, 1592, 1277, 702, cm−1; HRMS (m/z): acetate, 80:20 v/v): H NMR (400 MHz, CDCl3) δ 7.51 (t, J = 8.4
[M+H]+ calcd for C26H16 Cl2O3N2: 475.3250; found: 475.0609.
Hz, 4H), 7.19-7.35 (m, 5H), 6.82-7.03 (m, 5H), 6.41-6.52 (m,
benzoyl) 2H), 6.29 (s, 2H), 1.27 (s, 9H); 0.99 (s, 9H); 13C NMR (100 MHz,
(Z)-2-Amino-5-chloro-4-((4-chloro-2-(2-fluoro
phenyl)imino)-3-(2-fluorobenzoyl)cyclohexa-2,5-dien-1-one
CDCl3) δ 196.6, 195.6, 182.7, 157.1, 156.6, 155.3, 150.1, 144.7,
o
(2c): Dark red colour soild; mp 161-163 C, Rf 0.67; (hexanes : 136.7, 134.5, 131.2, 131.0, 130.1, 129.8, 129.6, 129.4, 128.7,
ethyl acetate, 70:30 v/v): 1H NMR (400 MHz, DMSO-d6) δ 8.38 125.3, 124.6, 123.1, 120.5, 111.6, 35.1, 34.7, 31.1, 31.0; IR
(s 2H), 7.55 (q, J = 6.8 Hz, 1H), 7.46 (q, J = 6.3 Hz, 1H), 7.23- (neat) 3434, 2250, 2123, 1659, 1027, 824, 763, 625, cm−1;
7.37 (m, 3H), 7.09-7.22 (m, 3H), 7.00-7.09 (m, 2H), 6.81 (t, J = HRMS (m/z): [M+H]+ calcd for C34H34O3N2: 518.6570; found:
7.2 Hz, 1H), 6.43 (d, J = 8Hz, 1H); 13C NMR (100 MHz, DMSO- 518.6469.
d6) δ 189.0, 187.1, 179.5, 159.9 (d, 1JC-F = 252 Hz), 158.8 (d, 1JC- (E)-3-Acetyl-4-((2-acetylphenyl)imino)-2-amino cyclo hexa-
3
o
= 251 Hz), 154.9, 148.8, 146.6, 134.1(d, J
= 9.3 Hz,2C), 2,5-dien-1-one (2h): Dark red colour soild; mp 121-123 C, Rf
F
C-F
1
132.2, 130.3, 129.5, 129.4, 129.1, 128.9, 128.2, 127.4, 127.2, 0.53; (hexanes : ethyl acetate, 70:30 v/v): H NMR (400 MHz,
125.7, 124.6, 124.4, 122.4, 116.4(d, 2J C-F = 10.8 Hz), 116.2(d, J DMSO-d6) δ 8.46 (s, 2H), 7.86 (dd, J = 7.6 Hz, J = 1.2 Hz, 1H),
2
= 21.1 Hz), 104; IR (neat) 3435, 2924, 2359, 1663, 1581, 1291, 7.54 (td, J = 1.2 Hz, J = 7.2 Hz,1H), 7.24 (td, J = 1.2 Hz, J = 7.6
758, cm−1; HRMS (m/z): [M+H]+ calcd for C26H14Cl2O3F2N2Na: Hz, 1H), 6.85 (d, J = 10 Hz, 1H), 6.74 (dd, J = 7.8 Hz, J = 0.8Hz,
533.0242; found: 533.0242.
(Z)-2-Amino-5-chloro-4-((4-chloro-2-(2-chloro
1H), 6.63 (d, J = 10 Hz, 1H), 2.55 (s, 3H), 2.44 (s , 3H); 13C NMR
(100 MHz, DMSO-d6) δ 200.7, 198.9, 182.6, 155.1, 149.2,
benzoyl))imino)-3-(2-chlorobenzoyl)cyclohexa-2,5-dien-1-one 147.9, 132.6, 131.9, 129.9, 128.9, 123.9, 121.1, 107.9, 33.2,
o
(2d): Dark red colour soild; mp 148-150 C, Rf 0.47; (hexanes 29.9; IR (neat) 3455, 2252, 2125, 1658, 1025, 824, 764, 625
:ethyl acetate, 70:30 v/v): 1H NMR (400 MHz, DMSO-d6) δ cm−1; HRMS (m/z): [M+H]+ calcd for C16H14O3N2Na: 305.0897;
8.48 (s, 2H), 7.41-7.50 (m, 2H), 7.30-7.41 (m, 3H), 7.23-7.31 (m, found: 305.0897.
2H), 7.09-7.24 (m, 3H), 6.84 (d, J = 7.2 Hz, 1H), 6.45 (d, J = 8.8 (E)-2-Amino-3-(cyclohexanecarbonyl)-4-((2-(cyclo
Hz, 1H); 13C NMR (100 MHz, DMSO-d6) δ 191.7, 190.3, 179.6, hexanecarbonyl)phenyl)imino)cyclohexa-2,5-dien-1-one (2i):
149.3, 146.9, 138.4, 137.8, 132.9, 132.1, 131.9, 130.4, 130.12, Red colour soild; mp 128-130 oC, Rf 0.5; (hexanes : ethyl
1
130.03, 130.00, 129.9, 129.6, 129.3, 128.6, 128.4, 127.3, 127.1, acetate, 90:10 v/v): H NMR (400 MHz, CDCl3) δ 7.75 (s, 1H),
121.2, 105.3; IR (neat) 3423, 2255, 1645, 1240, 1026, 1001, 7.62 (d, J = 0.8 Hz, 1H), 7.37 (td, J = 1.2Hz, J = 7.4 Hz,1H), 7.12
826, 765, cm−1; HRMS (m/z): [M+H]+ calcd for C26H14 (td, J = 1.2 Hz, J = 4 Hz, 1H), 6.83 (d, J = 10 Hz, 1H), 6.57 (d, J =
Cl4O3N2Na: 564.9657 ; found: 564.9651
7.2 Hz, 1H), 6.43 (d, J = 10 Hz, 1H), 3.68 (t , J = 11.2 Hz,1H),
(E)-2-Amino-3-(4-methylbenzoyl)-4-((2-(4-methyl
3.01 (t , J = 11.2 Hz,1H), 1.5-1.92 (m , 10H) 1.0-1.42 (m , 10H);
benzoyl)phenyl)imino)cyclohexa-2,5-dien-1-one (2e): Dark 13C NMR (100 MHz, CDCl3) δ 208.2, 205.8, 182.6, 155.6,
red colour soild; mp 118-120 oC, Rf 0.5; (hexanes : ethyl 149.3, 147.0, 131.8, 131.6, 129.5, 129.2, 128.9, 123.9, 120.5,
1
acetate, 80:20 v/v): H NMR (400 MHz, CDCl3) δ 7.36 (dd, J = 108.8, 49.6, 48.4, 29.4, 28.9, 26.1, 25.9, 25.8, 25.7; IR (neat)
5.4 Hz, J = 27.2 Hz, 3H), 7.12-7.28 (m, 2H), 6.91-7.12 (m, 2H), 3405, 1655, 1579, 1269, 1118, cm−1; HRMS (m/z): [M+H]+ calcd
6.87 (d, J = 9.6 Hz, 1H), 6.70 (d, J = 5.6 Hz, 2H), 6.46 (d, J = 7.6 for C16H14O3N2Na: 305.0897; found: 305.0897.
Hz, 1H), 6.27 (s, 1H), 2.31 (s, 3H) 2.01 (s, 3H); 13C NMR (100 (E)-2-Amino-3-propionyl-4-((2-propionylphenyl)
MHz, CDCl3) δ 196.7, 196.0, 182.6, 156.8, 149.1, 144.5, 143.7, imino)cyclohexa-2,5-dien-1-one (2j): Dark red colour
142.0, 136.9, 134.6, 130.8, 130.6, 130.2, 129.7, 128.9, 128.8, soild; mp 123.5-124.5 oC, Rf 0.6; (hexanes : ethyl
1
128.4, 123.3, 120.2, 111.4, 42.5, 40.7, 21.6, 21.3; IR (neat) acetate, 75:25 v/v): H NMR (400 MHz, CDCl3) δ 8.09 (s,
3362, 2925, 2856, 1658, 1605, 1267, 794 cm−1; HRMS (m/z): 2H), 7.75 (dd, J = 1.2 Hz, J = 7.6Hz, 1H), 7.44 (td, J = 1.2
[M+H]+ calcd for C28H22O3N2: 434.1630; found: 435.1699.
Hz, J = 7.6 Hz,1H), 7.19 (td, J = 7.6 Hz, 1H), 6.90 (d, J = 10
(E)-2-Amino-3-(4-ethylbenzoyl)-4-((2-(4-ethyl
benzoyl) Hz, 1H), 6.61 (d, J = 8Hz, 1H), 6.50(d, J = 10 Hz, 1H), 2.55
phenyl)imino)cyclohexa-2,5-dien-1-one (2f): Dark red colour (s, 3H), 1.07-1.15 (m, 6H), 2.44 (s , 3H);; 13C NMR (100
o
soild; mp 119-121 C, Rf 0.47; (hexanes : ethyl acetate, 80:20 MHz, CDCl3) δ 205.3,202.7, 182.8, 155.4, 149.3, 147.6,
v/v): 1H NMR (400 MHz, CDCl3) δ 7.44 (dd, J = 8 Hz, J = 27.6 Hz, 132.1, 129.5, 129.3, 129.3, 124.1, 120.8, 108.9, 38.2,
4H), 7.27 (t, J = 7.6Hz, 1H), 7.21 (t, J = 9.6 Hz, 1H), 7.10 (d, J = 35.1, 9.0, 8.5; IR (neat) 3441, 2976, 2365, 1633, 1585
8.4 Hz, 2H), 6.99 (t, J = 7.6 Hz, 1H), 6.90 (d, J = 10.4 Hz, 1H), cm−1; HRMS (m/z): [M+H]+ calcd for C18H118O3N2:
6.74 (d, J = 8 Hz, 2H), 6.43-6.53 (m, 2H), 6.26 (s, 2H), 2.63 (q, J 310.3530; found: 310.3170.
= 7.6 Hz, 2H), 2.30 (q, J = 7.6 Hz, 2H), 1.20 (t, J = 7.6 Hz, 3H), (E)-2-Amino-3-isobutyryl-4-((2-
isobutyrylphenyl)
0.95(t, J = 7.6 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 196.9, imino) cyclohexa-2,5-dien-1-one (2k): Dark red colour
o
196.1, 182.8, 157.0, 150.0, 149.6, 148.4, 144.8, 137.3, 135.0, soild; mp 126-128 C, Rf 0.35; (hexanes : ethyl acetate,
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131.2, 130.8, 130.5, 129.7, 129.4, 129.3, 129.3, 127.8, 127.3, 80:20 v/v): H NMR (400 MHz, DMSO-d6) δ 8.15(s, 2H),
123.4, 120.4, 111.6, 29.1, 28.8, 15.3, 15.0; IR (neat) 3490, 7.98 (dd, J = 0.8 Hz, J = 7.8 Hz, 1H), 7.74 (dd, J = 1.6 Hz, J
2925, 2857, 1620, 1456, 757cm−1; HRMS (m/z): [M+H]+ calcd = 7.6 Hz, 1H), 7.70 (dd, J = 1.2 Hz, J = 8 Hz,1H), 7.44-7.60
for C30H26O3N2Na: 485.1837; found: 485.1836.
(m, 2H), 7.23 (td, J = 1.2 Hz, J = 7.6Hz, 1H), 7.21 (t, J =
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