Page 7 of 10
COMMUNICATION
RSC Advances
DOI: 10.1039/C4RA03655G
= 5.1Hz), 7.01 (s, 1H), 7.04ꢀ7.09 (m, 2H), 7.78 (s, 1H), 7.82 (s, 1H);
TOFꢀMS m/z 621.1807 [M+23] +, Anal. Calcd for C30H34N2O7S2: C,
60.18; H, 5.72; N, 4.68 Found: C, 60.34; H, 5.78; N, 4.71.
2-((3E,5E)-3,5-bis(2,4-dichlorobenzylidene)-4-oxopiperidin-1-yl)-
2-oxoethylmorpholine-4-carbodithioate (4i):
Yield: 75% (pale yellow solid); mp 163ꢀ164oC; IR (CHCl3, cmꢀ1):
3062, 2917, 2855, 2364, 1653, 1616, 1467, 1271, 1233, 995, 844; 1H
NMR (400MHz, CDCl3): δ 3.73ꢀ3.88 (m, 6H), 4.14 (s, 4H), 4.74 (s,
4H), 7.22 (d, 1H,J = 8.8Hz), 7.30 (d, 1H, J = 7.3Hz), 7.32 (d, 1H, J
2-((3E,5E)-3,5-bis(2-chlorobenzylidene)-4-oxopiperidin-1-yl)-2-
oxoethylmorpholine-4-carbodithioate (4c):
Yield: 71% (yellow solid); mp 190ꢀ191oC; IR (CHCl3, cmꢀ1): 2954, = 8.8Hz), 7.37 (d, 1H, J = 8.8Hz), 7.48 (s, 1H), 7.52 (s, 1H), 7.93 (s,
2902, 2863, 2362, 1654, 1620, 1460, 1269, 994, 755; 1H NMR 2H); TOFꢀMS m/z 636.9826 [M+23]
, Anal. Calcd for
+
(400MHz, CDCl3): δ 3.71(s, 4H), 3.90 (brs, 2H), 4.19 (s, 4H), 4.77 C26H22Cl4N2O3S2: C, 50.66; H, 3.60; N, 4.54. Found: C, 50.58; H,
(d, 4H, J = 6.6Hz), 7.31ꢀ7.5 (m, 4H), 7.40ꢀ7.48 (m, 4H), 8.02 (s, 3.71; N, 4.60.
2H); TOFꢀMS m/z 569.0605 [M+23]+, Anal. Calcd for
C26H24Cl2N2O3S2: C, 57.04; H, 4.42; N, 5.12. Found: C, 57.31; H,
4.48; N, 5.01
2-((3E,5E)-3,5-bis(4-fluorobenzylidene)-4-oxopiperidin-1-yl)-2-
oxoethylmorpholine-4-carbodithioate (4j):
Yield: 69% (pale yellow solid); mp 163ꢀ164oC; IR (CHCl3, cmꢀ1):
2972, 2856, 2365, 1647, 1599, 1414, 1269, 1234, 990,840; 1H NMR
(400MHz, CDCl3): δ 3.73(s, 4H), 3.88 (brs, 2H), 4.19 (s, 4H), 4.91
2-((3E,5E)-3,5-bis(4-chlorobenzylidene)-4-oxopiperidin-1-yl)-2-
oxoethylmorpholine-4-carbodithioate (4d):
Yield: 74% (pale yellow solid); mp 178ꢀ179oC; IR (CHCl3, cmꢀ1): (s, 4H), 7.10 (d, 1H, J = 8.8Hz), 7.14 (d, 1H, J = 2.9Hz), 7.18 (d, 2H,
2938, 2364, 1654, 1602, 1507, 1297, 808; 1HNMR (400MHz, J = 8.0Hz), 7.43ꢀ7.45 (m, 4H), 7.79 (s, 1H), 7.83 (s, 1H); TOFꢀMS
CDCl3): δ 3.71 (t, 4H, J = 5.1Hz), 3.91 (brs, 2H), 4.18 (s, 4H), 4.90 m/z 537.1196 [M+23]+, Anal. Calcd for C26H24F2N2O3S2: C, 60.68;
(s, 4H), 7.36 (d, 2H, J = 8.8Hz), 7.40ꢀ7.46 (m, 6H), 7.77 (s, 1H), H, 4.70; N, 5.44. Found: C, 60.62; H, 4.67; N, 5.52.
7.82 (s, 1H); TOFꢀMS m/z 569.0605 [M+23] +, Anal. Calcd for
C26H24Cl2N2O3S2: C, 57.04; H, 4.42; N, 5.12. Found: C, 57.28; H,
4.43; N, 5.07
2-((3E,5E)-3,5-bis(3-fluorobenzylidene)-4-oxopiperidin-1-yl)-2-
oxoethylmorpholine-4-carbodithioate (4k):
Yield: 71% (pale yellow solid); mp 198ꢀ199oC; IR (CHCl3, cmꢀ1):
1
2853, 2364, 1653, 1617, 1430, 1269, 1227, 996, 779; HNMR (400
2-((3E,5E)-3,5-bis(3-chlorobenzylidene)-4-oxopiperidin-1-yl)-2-
MHz, CDCl3): δ 3.71(t, 4H, J = 4.4Hz), 3.91 (brs, 2H), 4.18 (s, 4H),
oxoethylmorpholine-4-carbodithioate (4e):
Yield: 72% (yellow solid); mp 181ꢀ182oC; IR (CHCl3, cmꢀ1): 2965, 4.92 (s, 4H), 7.10ꢀ7.16 (m, 4H), 7.20ꢀ7.25 (m, 2H), 7.39ꢀ7.46 (m,
1
+
2923, 2859, 2362, 1638, 1610, 1458, 1269, 997, 790, 684; H NMR 2H),7.78 (s, 1H), 7.83 (s, 1H); TOFꢀMS m/z 537.1196 [M+23] ,
(400MHz, CDCl3): δ 3.71 (s, 4H), 3.89 (brs, 2H), 4.17 (s, 4H), 4.91 Anal. Calcd for C26H24F2N2O3S2: C, 60.68; H, 4.70; N, 5.44. Found:
(s, 4H), 7.31ꢀ7.40 (m, 8H), 7.75 (s, 1H), 7.80 (s, 1H); TOFꢀMS m/z C, 60.62; H, 4.69; N, 5.51.
569.0605 [M+23]+, Anal. Calcd for C26H24Cl2N2O3S2: C, 57.04; H,
2-((3E,5E)-3,5-bis(3,5-difluorobenzylidene)-4-oxopiperidin-1-yl)-
4.42; N, 5.12. Found: C, 57.29; H, 4.45; N, 5.05
2-oxoethylmorpholine-4-carbodithioate (4l):
Yield: 70% (pale yellow solid); mp 205ꢀ206oC; IR (CHCl3, cmꢀ1):
1
3065, 2864,2365, 1641, 1618, 1430, 1265, 1238, 994, 858; HNMR
2-((3E,5E)-3,5-bis(4-bromobenzylidene)-4-oxopiperidin-1-yl)-2-
(400MHz, CDCl3): δ 3.72(t, 4H, J = 4.4Hz), 3.91 (brs, 2H), 4.18 (s,
oxoethylmorpholine-4-carbodithioate (4f):
Yield: 77% (pale yellow solid); mp 237ꢀ238oC; IR (CHCl3, cmꢀ1): 4H), 4.89 (d, 4H, J = 8.0Hz), 6.84 (d, 1H, J = 8.8Hz), 6.88 (d, 1H, J
2920, 2963, 2851, 2365, 1654, 1609, 1487, 1267, 824; 1HNMR (400 = 8.0Hz), 6.93 (d, 2H, J = 5.9Hz), 6.97 (d, 2H, J = 5.9Hz), 7.71 (s,
MHz, CDCl3): δ 3.71 (brs, 4H), 3.88 (s, 2H), 4.20 (s, 4H), 4.89 (s, 1H), 7.76 (s, 1H); TOFꢀMS m/z 573.1008 [M+23] +, Anal. Calcd for
4H), 7.29 (d, 2H, J = 8.8Hz), 7.33 (d, 2H, J = 8.0Hz), 7.56 (d, 2H, J C26H22F4N2O3S2: C, 56.72; H, 4.03; N, 5.09. Found: C, 56.79; H,
= 8.0Hz), 7.61 (d, 2H, J = 8.0Hz), 7.75 (s, 1H), 7.80 (s, 1H); TOFꢀ 4.14; N, 5.02.
MS m/z 656.9595 [M+23]+, Anal. Calcd for C26H24Br2N2O3S2: C,
49.07; H, 3.80; N, 4.40. Found: C, 49.09; H, 3.69; N, 4.51.
2-((3E,5E)-3,5-bis(4-methylbenzylidene)-4-oxopiperidin-1-yl)-2-
oxoethylmorpholine-4-carbodithioate (4g):
2-oxo-2-((3E,5E)-4-oxo-3,5-bis(3,4,5-trimethoxybenzylidene)
piperidin-1-yl)ethylmorpholine-4-carbodithioate (4m) :
o
Yield: 72% (pale yellow solid); mp 181ꢀ182 C; IR (CHCl3, cmꢀ1):
Yield: 81% (pale yellow solid); mp 158ꢀ159oC; IR (CHCl3, cmꢀ1): 2938, 2839, 2365, 1642, 1605, 1505, 1419, 1252, 997, 836; 1H NMR
2855, 2364, 1602, 1430, 1265, 992, 815; 1HNMR (400 MHz, (400 MHz, CDCl3): δ 3.71 (t, 4H, J = 5.1Hz), 3.91ꢀ3.98 (m, 20H),
CDCl3): δ 2.38 (s, 3H), 2.41 (s, 3H), 3.69 (t, 4H, J = 5.1Hz), 3.89 4.23 (s, 4H), 4.96 (s, 2H), 4.99 (s, 2H), 6.65 (s, 2H), 6.71 (s, 2H),
(brs, 2H), 4.19 (s, 4H), 4.93 (d, 4H, J = 4.4Hz), 7.22 (d, 2H, J = 7.77 (s, 1H), 7.80 (s, 1H); TOFꢀMS m/z 681.2019 [M+23] +, Anal.
7.3Hz), 7.28 (d, 2H, J = 7.3Hz), 7.33 (d, 2H, J = 8.0Hz), 7.37 (d, 2H, Calcd for C32H38N2O9S2: C, 58.34; H, 5.81; N, 4.25. Found: C,
J = 8.0Hz), 7.80 (s, 1H), 7.85 (s, 1H); TOFꢀMS m/z 529.0775 58.42; H, 5.76; N, 4.31.
[M+23] +, Anal. Calcd for C28H30N2O3S2: C, 66.37; H, 5.97; N, 5.53.
Found: C, 66.42; H, 5.93; N, 5.60.
2-oxo-2-((3E,5E)-4-oxo-3,5-bis(2-(trifluoromethyl)benzylidene)
piperidin-1-yl)ethylmorpholine-4-carbodithioate (4n):
Yield: 79% (pale yellow solid); mp 184ꢀ185oC; IR(CHCl3, cmꢀ1):
2857, 2363, 1654, 1618, 1430, 1315, 1163, 991, 771; 1HNMR
2-((3E,5E)-3,5-bis(4-ethylbenzylidene)-4-oxopiperidin-1-yl)-2-
oxoethyl morpholine-4-carbodithioate (4h):
Yield: 76% (pale yellow solid); mp 161ꢀ162oC; IR (CHCl3, cmꢀ1): (400MHz, CDCl3): δ 3.72 (t, 4H, J = 5.1Hz), 3.91 (brs, 2H), 4.06 (s,
2965, 2929, 2850, 2365, 1654, 1603, 1458, 1268, 1228, 996, 828; 4H), 4.64 (s, 4H), 7.33 (d, 1H, J = 7.3Hz), 7.46 (d, 2H, J = 7.3Hz),
1HNMR (400MHz, CDCl3): δ 1.23ꢀ1.29 (m, 6H), 2.65ꢀ2.73 (m, 4H), 7.54ꢀ7.65 (m, 3H), 7.73 (d, 1H, J = 8.0Hz), 7.79 (d, 1H, J = 7.3Hz),
3.69 (t, 4H, J = 5.1Hz), 3.93 (brs, 2H), 4.20 (s, 4H), 4.94 (s, 4H), 8.05 (s, 1H), 8.09 (s, 1H); 13CꢀNMR (100MHz, CDCl3): δ39.24,
7.24 (s, 1H), 7.30 (d, 2H, J = 8.0Hz), 7.36 (d, 3H, J = 8.0Hz), 7.40 43.18, 46.67, 65.92, 125.76, 126.77, 127.91, 128.21, 130.09, 131.23,
(d, 2H, J = 8.0Hz), 7.82 (s, 1H), 7.86 (s, 1H); TOFꢀMS m/z 557.2011 133.13, 134.62, 165.96, 185.59, 194.63; TOFꢀMS m/z 637.1133
[M+23] +, Anal. Calcd for C30H34N2O3S2: C, 67.38; H, 6.41; N, 5.24. [M+23] , Anal. Calcd for C28H24F6N2O3S2: C, 54.72; H, 3.94; N,
+
Found: C, 67.29; H, 6.34; N, 5.28.
4.56. Found: C, 54.78; H, 3.87; N, 4.61.
6 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 2012