Please do not adjust margins
RSC Advances
Page 12 of 18
DOI: 10.1039/C5RA25853G
ARTICLE
Journal Name
(3E,5E)-N-butyl-3,5-bis(2-fluorobenzylidene)-4-oxopiperidine- 50.6, 35.8, 26.2, 24.7, 18.8; ESI-MS: m/z 419 (M+H+); HRMS
1-carbothioamide (38)
(ESI): m/z calculated for C26H30N2OS + H+ (M+H+): 419.2157.
The title compound was synthesized from (3E,5E)-3,5-bis(2- Found: 419.2158. Elemental analysis (%) for C26H30N2OS:
fluorobenzylidene)piperidin-4-one ( ) and butyl isothiocyanate Calcd.: C, 74.60; H, 7.22; N, 6.69; Found, C, 74.33; H, 7.42; N,
in 71% yield as yellow solid. mp: 163-165 °C; IR (KBr)
(cm-1): 6.96.
3418, 3120, 1621, 1384, 1215, 757; 1H NMR (400 MHz, CDCl3): (3E,5E)-N-butyl-3,5-bis(4-methoxybenzylidene)-4-
7.89 (s, 2H), 7.47–7.40 (m, 4H), 7.28–7.24 (m, 2H), 7.21–7.16 oxopiperidine-1-carbothioamide (42)
(m, 2H), 5.13 (s, 1H), 4.97 (s, 4H), 3.48–3.43 (m, 2H), 1.34–1.27 The title compound was synthesized from (3E,5E)-3,5-bis(4-
(m, 2H), 1.14–1.07 (m, 2H),0.82 (t, J = 7.3 Hz, 3H); 13C (100 fluorobenzylidene)piperidin-4-one
12 and butyl
MHz, CDCl3): 186.2, 182.2, 161.9, 159.4, 133.2, 131.7, 131.6, isothiocyanate in 80% yield as yellow solid. mp: 164-166 °C; IR
130.9, 130.9, 130.8, 124.5, 124.4, 122.2, 122.1, 116.2, 116.0, (KBr)
(cm-1): 3410, 3020, 1635, 1390, 1215, 1030; 1H NMR
8
ν
δ
(
)
δ
ν
48.8, 46.1, 30.7, 19.8, 13.7; ESI-MS: m/z 427 (M+H+); HRMS (400 MHz, CDCl3):
δ 7.80 (s, 2H), 7.44 (d, J = 8.8 Hz, 4H), 7.01
(ESI): m/z calculated for C24H24F2N2OS + H+ (M+H+): 427.1656. (d, J = 8.8 Hz, 4H), 5.09 (d, J = 1.0 Hz, 4H), 4.99 (s, 1H), 3.88 (s,
Found: 427.1654. Elemental analysis (%) for C24H24F2N2OS: 6H), 3.45–3.41 (m, 2H), 1.25–1.18 (m, 2H), 1.11–1.02 (m,
Calcd.: C, 67.58; H, 5.67; N, 6.57; Found, C, 67.30; H, 5.98; N, 2H),0.79 (t, J = 7.2 Hz, 3H); 13C (100 MHz, CDCl3):
δ
186.9, 182.2,
160.8, 137.5, 132.4, 129.7, 126.9, 114.4, 55.4, 48.8, 46.1, 30.7,
(3E,5E)-N-butyl-3,5-bis(4-fluorobenzylidene)-4-oxopiperidine- 19.8, 13.7; ESI-MS: m/z 451 (M+H+); HRMS (ESI): m/z
1-carbothioamide (39)
calculated for C26H30N2O3S + H+ (M+H+): 451.2055. Found:
The title compound was synthesized from (3E,5E)-3,5-bis(4- 451.2055. Elemental analysis (%) for C26H30N2O3S: Calcd.: C,
fluorobenzylidene)piperidin-4-one ( ) and butyl isothiocyanate 69.30; H, 6.71; N, 6.22; Found, C, 69.41; H, 6.99; N, 6.00.
in 81% yield as yellow solid. mp: 176-178 °C; IR (KBr)
(cm-1): (3E,5E)-N-butyl-3,5-bis(4-isopropylbenzylidene)-4-
3408, 3090, 1640, 1385, 1215, 768; 1H NMR (400 MHz, CDCl3): oxopiperidine-1-carbothioamide (43)
7.81 (s, 2H), 7.47 (d/d, J1= 5.3 Hz, J2= 8.7 Hz, 4H), 7.21–7.17 The title compound was synthesized from (3E,5E)-3,5-bis(4-
(m, 4H), 5.07 (d, J = 1.12 Hz, 4H), 5.03 (s, 1H), 3.47–3.42 (m, isopropylbenzylidene)piperidin-4-one 13 and butyl
2H), 1.30–1.23 (m, 2H), 1.14–1.04 (m, 2H),0.81 (t, J = 7.2 Hz, isothiocyanate in 77% yield as yellow solid. mp: 116-118 °C; IR
3H); 13C (100 MHz, CDCl3+DMSO-d6): (cm-1): 3411, 3019, 1640, 1218; 1H NMR (400 MHz,
191.9, 187.1, 168.7, (KBr)
166.7, 140.4, 140.3, 137.7, 136.7, 135.7, 120.7, 120.6, 53.3, CDCl3): 7.83 (s, 2H), 7.41 (d, J = 8.2 Hz, 4H), 7.35 (d, J = 8.2 Hz,
6.47.
9
ν
δ
(
)
δ
ν
δ
50.7, 35.8, 24.7, 18.7; ESI-MS: m/z 427 (M+H+); HRMS (ESI): 4H), 5.10 (d, J = 1.1 Hz, 4H),4.92 (s, 1H), 3.43–3.38 (m, 2H),
m/z calculated for C24H24F2N2OS + H+ (M+H+): 427.1656. Found: 3.03–2.93 (m, 2H),1.30 (d, J = 6.9 Hz, 12H), 1.20–1.11 (m, 2H),
427.1658. Elemental analysis (%) for C24H24F2N2OS: Calcd.: C, 1.09–1.02 (m, 2H), 0.78 (t, J = 7.2 Hz, 3H); 13C (100 MHz,
67.58; H, 5.67; N, 6.57; Found, C, 67.90; H, 5.81; N, 6.30.
(3E,5E)-N-butyl-3,5-bis(2-methylbenzylidene)-4-
oxopiperidine-1-carbothioamide (40)
CDCl3): δ187.2, 182.1, 151.1, 137.9, 131.8, 130.9, 130.6, 127.1,
48.8, 45.9, 34.0, 30.6, 23.7, 19.7, 13.7; ESI-MS: m/z 475
(M+H+); HRMS (ESI): m/z calculated for C30H38N2OS + H+
The title compound was synthesized from (3E,5E)-3,5-bis(2- (M+H+): 475.2783. Found: 475.2782. Elemental analysis (%) for
methylbenzylidene)piperidin-4-one
isothiocyanate in 71% yield as yellow solid. mp: 152-154 °C; IR H, 8.31; N, 5.63.
(KBr)
(cm-1): 3410, 3019, 1620, 1215; 1H NMR (400 MHz, (3E,5E)-3,5-bis(2-fluorobenzylidene)-1-(4-phenylthiazol-2-
CDCl3): 8.00 (s, 2H), 7.37–7.24 (m, 8H), 4.92 (d, J = 1.2 Hz, yl)piperidin-4-one (44)
4H), 4.86 (s, 1H), 3.42 (q, J1 = 7.0 Hz, J2 = 11.8, 2H),2.39 (s, 6H), The title compound was synthesized from (3E,5E)-3,5-bis(2-
1.25–1.18 (m, 2H), 1.10–1.01 (m, 2H), 0.80 (t, J = 7.2 Hz, 3H); fluorobenzylidene)piperidin-4-one and phenacyl
13C (100 MHz, CDCl3):
187.2, 181.8, 138.2, 137.3, 133.2, thiocyanate in 73% yield as yellow solid. mp: 110-112 °C; IR
131.9, 130.7, 129.6, 128.9, 126.0, 48.4, 46.0, 30.7, 20.1, 19.8, (KBr)
(cm-1): 3109, 1620, 1454, 1218, 761; 1H NMR (400 MHz,
13.7; ESI-MS: m/z 419 (M+H+); HRMS (ESI): m/z calculated for CDCl3):
7.97 (s, 2H), 7.60 (d, J = 6.8, 2H), 7.48–7.44 (m, 4H),
C26H30N2OS
H+ (M+H+): 419.2157. Found: 419.2154. 7.32–7.26 (m, 4H), 7.25–7.19 (m, 3H), 6.73 (s, 1H), 4.79 (s, 4H);
Elemental analysis (%) for C26H30N2OS: Calcd.: C, 74.60; H, 7.22; 13C (100 MHz, DMSO-d6):
186.2, 169.2, 162.0, 159.6, 150.9,
(
10)
and
butyl C30H38N2OS: Calcd.: C, 75.90; H, 8.07; N, 5.90; Found, C, 76.11;
ν
δ
(8)
δ
ν
δ
+
δ
N, 6.69; Found, C, 74.50; H, 7.52; N, 6.99.
(3E,5E)-N-butyl-3,5-bis(4-methylbenzylidene)-4-
oxopiperidine-1-carbothioamide (41)
134.5, 134.5, 132.4, 132.3, 131.6, 130.6, 130.6, 128.8, 128.0,
125.9, 125.1, 125.1, 122.6, 122.5, 116.4, 116.2, 104.8, 50.1;
ESI-MS: m/z 471 (M+H+); Elemental analysis (%) for
The title compound was synthesized from (3E,5E)-3,5-bis(4- C28H20F2N2OS: Calcd.: C, 71.47; H, 4.28; N, 5.95; Found, C,
methylbenzylidene)piperidin-4-one 11 and butyl 71.72; H, 4.49; N, 6.28.
isothiocyanate in 75% yield as yellow solid. mp: 194-196 °C; IR (3E,5E)-3,5-bis(4-fluorobenzylidene)-1-(4-phenylthiazol-2-
(KBr)
(cm-1): 3411, 3019, 1644, 1215; 1H NMR (400 MHz, yl)piperidin-4-one (45)
CDCl3): 7.83 (s, 2H), 7.37 (d, J = 8.1 Hz, 4H), 7.29 (d, J = 8.1 Hz, The title compound was synthesized from (3E,5E)-3,5-bis(4-
4H), 5.09 (d, J = 1.1 Hz, 4H),4.93 (s, 1H), 3.41 (q, J1 = 7.0 Hz, J2 = fluorobenzylidene)piperidin-4-one and phenacyl
11.7 Hz, 2H), 2.43 (s, 6H),1.21–1.14 (m, 2H), 1.09–0.99 (m, 2H), thiocyanate in 75% yield as yellow solid. mp: 191-193 °C; IR
0.78 (t, J = 7.2 Hz, 3H); 13C (100 MHz, CDCl3+DMSO-d6): (cm-1): 3021, 1626, 1406, 1216, 762; 1H NMR (400 MHz,
191.9, (KBr)
(
)
ν
δ
(9)
δ
ν
187.1, 144.4, 141.3, 141.2, 136.7, 136.5, 135.7, 134.4, 53.6, CDCl3):
δ
7.88 (s, 2H), 7.63 (d, J = 6.9, 2H), 7.50 (d/d, J1 = 5.4 Hz,
12 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins