Arkivoc 2017, part ii, 546-556
Piętka-Ottlik, M. et al
4,5), 7.63 (d, J 8.6 Hz, 2H, ArH-6), 7.76-7.82 (m, 4H, PhH-6, ArH-2), 7.96 (d, J 7.2 Hz, 2H, PhH-3), 10.61 (s, 2H,
13
NH). C NMR (151 MHz, DMSO-d6): δC 19.81 (CH3), 119.64 (CH), 122.83 (CH), 126.37 (CH), 128.01 (C), 128.62
(CH), 128.93 (CH), 130.14 (CH), 131.99 (C), 132.07 (CH), 133.45 (C), 135.54 (C), 137.48 (C), 166.26 (C=O). HRMS
(TOF MS ESI): m/z for (C28H21Cl2N2O2Se2 + Na)+ calculated: 668.9297, 670.9284, 672.9272; found: 668.9341,
670.9288, 672.9265.
Bis[2-(5-chloro-2-methoxyphenylcarbamoyl)]phenyl diselenide (6e). Grey powder, yield 85%, mp 194–195 oC
1
(from methylene chloride); H NMR (300 MHz, DMSO-d6): δH 3.86 (s, 6H, OCH3), 7.15 (d, J 8.9 Hz, 2H, ArH-3),
7.29 (dd, J 2.6 Hz, J 8.8 Hz, 2H, ArH-4), 7.38-7.51 (m, 4H, PhH-4,5), 7.78 (d, J 7.8 Hz, 2H, PhH-6), 7.84 (d, J 2.6
Hz, 2H, ArH-6), 7.99 (d, J 7.5 Hz, 2H, PhH-3), 9.93 (s, 2H, NH). HRMS (TOF MS ESI): m/z for (C28H22Cl2N2O4Se2 +
H)+ calculated: 680.9363; found: 680.9400.
Bis[2-(2-chloro-5-methylphenylcarbamoyl)]phenyl diselenide (6g). White solid, yield 75%, mp 203–204 °C
1
(from methylene chloride); H NMR (300 MHz, DMSO-d6): δH 2.35 (s, 6H, CH3), 7.18 (dd, J 8.1 Hz, J 1.1 Hz, 2H,
ArH-4), 7.43-7.46 (m, 4H, PhH-5, ArH-6), 7.47 (d, J 8.2 Hz, 2H, ArH-3), 7.50 (dd, J 7.4 Hz, J 1.0 Hz, 2H, PhH-4),
7.80 (d, J 8.0 Hz, 2H, PhH-6), 8.06 (d, J 7.5 Hz, 2H, PhH-3), 10.36 (s, 2H, NH). 13C NMR (75 MHz, DMSO-d6): δC
20.4, 126.5, 126.7, 128.6, 128.7, 129.0, 129.3, 130.2, 132.3, 132.5, 132.6, 134.2, 137.3, 166.5. HRMS (TOF MS
ESI): m/z for (C28H21Cl2N2O2Se2 + Na)+ calculated: 670.9284; found: 670.9287.
Bis[2-(2-chloro-4-methylphenylcarbamoyl)]phenyl diselenide (6h). White powder, yield 62%, mp 260–261 °C
1
(from methylene chloride); H NMR (300 MHz, DMSO-d6): δH 2.35 (s, 6H, CH3), 7.23 (d, J 8.4 Hz, 2H, ArH-5),
7.40-7.51 (m, 8H, PhH-4,5, ArH-3,6), 7.77 (d, J 7.4 Hz, 2H, PhH-6), 8.05 (d, J 6.9 Hz, 2H, PhH-3), 10.35 (s, 2H,
NH). 13C NMR (151 MHz, DMSO-d6): δC 20.8, 126.9, 128.7, 129.0, 129.1, 130.1, 130.3, 130.6, 132.3, 132.7,
133.0, 133.1, 138.3, 167.0. HRMS (TOF MS ESI): m/z for (C28H22Cl2N2O2Se2 + H)+ calculated: 648.9465; found:
648.9327.
Bis[2-(5-chloro-2-methylphenylcarbamoyl)]phenyl diselenide (6j). White powder, yield 86%, mp 247–248 °C
1
(from 1,2-dichloroethane); H NMR (300 MHz, DMSO-d6): δH 2.28 (s, 6H, CH3), 7.28 (dd, J 8.3 Hz, J 2.2 Hz, 2H,
ArH-4), 7.34 (d, J 8.3 Hz, 2H, ArH-3), 7.40-7.52 (m, 4H, PhH-4,5), 7.53 (d, J 2.2 Hz, 2H, ArH-6), 7.80 (dd, J 7.8 Hz,
J 1.3 Hz, 2H, PhH-6), 8.02 (dd, J 7.4 Hz, J 1.4 Hz, 2H, PhH-3), 10.28 (s, 2H, NH). 13C NMR (75 MHz, DMSO-d6): δC
17.4, 125.85, 125.9, 126.4, 128.6, 129.8, 130.1, 131.9, 132.1, 132.3, 132.5, 132.9, 137.2, 166.5. HRMS (TOF MS
ESI): m/z for (C28H21Cl2N2O2Se2 + Na)+ calculated: 670.9284; found: 670.9291.
Bis[2-(3-methoxyphenylcarbamoyl)]phenyl diselenide (6k). White powder, yield 74%, mp 221–223 °C (from
1
methylene chloride); H NMR (300 MHz, DMSO-d6): δH 3.78 (s, 6H, OCH3), 6.74 (dd, J 8.2 Hz, J 1.7 Hz, 2H, ArH-
4), 7.30 (dd, J 8.2 Hz, J 8.1 Hz, 2H, ArH-5), 7.40 (dd, J 8.1 Hz, J 1.2 Hz, 2H, ArH-6), 7.42 (ddd, J 8.0 Hz, J 7.0 Hz, J
1.2 Hz, 2H, PhH-5), 7.45-7.48 (m, 4H, PhH-4, ArH-2), 7.81 (dd, J 8.0 Hz, J 1.1 Hz, 2H, PhH-6), 7.96 (dd, J 7.6 Hz, J
1.3 Hz, 2H, PhH-3), 10.54 (s, 2H, NH). 13C NMR (151 MHz, DMSO-d6): δC 55.0, 106.2, 109.5, 112.7, 126.4, 128.6,
129.5, 130.1, 131.9, 132.0, 133.7, 139.8, 159.4, 166.3. HRMS (TOF MS ESI): m/z for (C28H24N2O4Se2 + H)+
calculated: 612.0189; found: 612.0232.
Bis[2-(4-methoxyphenylcarbamoyl)]phenyl diselenide (6l). White powder, yield 62%, mp 285.5–287.5 °C
(from methylene chloride) (lit.35 290–292 °C; 1H NMR (300 MHz, DMSO-d6): δH 3.76 (s, 6H, OCH3), 6.97 (d, J 9.0
Hz, 4H, ArH-3,5), 7.40 (ddd, J 7.1 Hz, J 6.9 Hz, J 0.9 Hz, 2H, PhH-4), 7.44 (ddd, J 8.0 Hz, J 7.1 Hz, J 1.3 Hz, 2H,
PhH-5), 7.68 (d, J 9.0 Hz, 4H, ArH-2,6), 7.79 (dd, J 8.0 Hz, J 0.8 Hz, 2H, PhH-6), 7.95 (d, J 6.8 Hz, 2H, PhH-3),
10.44 (s, 2H, NH). 13C NMR (151 MHz, DMSO-d6): δC 55.7, 114.3, 122.7, 126.9, 129.0, 130.6, 132.2, 132.4,
132.5, 134.3, 156.4, 166.4. HRMS (TOF MS ESI): m/z for (C28H24N2O4Se2 + H)+ calculated: 612.0189; found:
612.01823.
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