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2020
C. IBIS¸ ET AL.
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1525 (NO2); UV (CHCl3): λ = 240, 393 nm; H NMR (500 MHz, CDCl3): ppm = 0.88
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(t, J = 6.83 Hz, 3H, CH3), 1.26–1.40 (m, 14H, (CH2)7; 3H, OCH2CH3), 1.64–1.70 (m,
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2H, SCH2CH2), 2.95 (t, J = 7.32 Hz, 2H, SCH2), 3.64 (bs, 8H, CH2piper), 4.19 (q, 2H,
OCH2); 13C NMR (125 MHz, CDCl3): ppm = 14.09 (CH3), 14.60 (OCH2CH3), 22.66,
28.71, 28.73, 29.03, 29.25, 29.37, 29.46, 31.86, 35.56 ((CH2)9), 43.29, 52.84 (NCH2), 62.12
(OCH2), 111.67 (CClBr), 118.87 (CCl), 128.14 (CNO2), 155.09 (C O), 169.22 (CSN);
C21H34BrCl2N3O4S (MW = 575.40 g/mol); Calcd C:% 43.84, H:% 5.96, N:% 7.30, S:%
5.57; Found C:% 44.10, H:% 6.22, N:% 7.10, S:% 5.26.
1-(4-Bromo-3,4-dichloro-1-(decylthio)-2-nitrobuta-1,3-dienyl)-4-
(2-methoxyphenyl)piperazine (7c)
Followed the typical procedure for 5a. Yield: 140 mg (48.5%); Orange thick oil; Rf
(CH2Cl2): 0.56; IR (neat, cm−1) = 3020 (C Harom), 2900 (C Haliph), 2815 (OCH3), 1595
(C C), 1285, 1520 (NO2); UV (CHCl3): λ = 245, 393 nm; 1H NMR (500 MHz, CDCl3):
ppm = 0.88 (t, 3J = 6.83 Hz, 3H, CH3), 1.26–1.44 (m, 14H, (CH2)7), 1.64–1.72 (m, 2H,
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SCH2CH2), 2.98 (t, J = 7.32 Hz, 2H, SCH2), 3.23 (s, 4H, CH2piper), 3.82–4.03 (m, 4H,
CH2piper), 3.88 (s, 3H, OCH3), 6.90–7.08 (m, 4H, C6H4); 13C NMR (125 MHz, CDCl3):
ppm = 13.07 (CH3), 21.65, 27.72, 28.04, 28.24, 28.37, 28.46, 28.81, 30.85, 34.54 ((CH2)9),
49.47, 52.56 (NCH2), 54.55 (OCH3), 110.26 (CClBr), 117.64 (CCl), 110.73, 120.15,
123.20, 127.46 (CHarom), 129.37 (CNO2), 139.45 (N-Carom), 151.33 (H3CO Carom), 168.27
(CSN); C25H36BrCl2N3O3S (MW = 609.46 g/mol); Calcd C:% 49.27, H:% 5.95, N:% 6.90,
S:% 5.26; Found C:% 49.54, H:% 5.90, N:% 7.14, S:% 5.47.
1-(4-Bromo-3,4-dichloro-1-(decylthio)-2-nitrobuta-1,3-dienyl)-4-
(4-fluorophenyl)piperazine (7d)
Followed the typical procedure for 5a. Yield: 166 mg (63%); Orange thick oil; Rf
(CHCl3): 0.45; IR (neat, cm−1) = 3020 (C Harom), 2900 (C Haliph), 1590 (C C), 1280,
1530 (NO2); UV (CHCl3): λ = 242, 394 nm; 1H NMR (500 MHz, CDCl3): ppm = 0.88 (t,
3J = 6.91 Hz, 3H, CH3), 1.26–1.41 (m, 16H, (CH2)7), 1.65–1.71 (m, 2H, SCH2CH2), 2.98
(t, 3J = 7.08 Hz, 2H, SCH2), 3.24 (s, 4H, CH2piper), 3.61–3.99 (m, 4H, CH2piper), 6.88–7.00
(m, 4H, C6H4); 13C NMR (125 MHz, CDCl3): ppm = 13.09 (CH3), 21.64, 27.70, 28.03,
28.23, 28.35, 28.45, 28.80, 30.85, 34.58 ((CH2)9), 49.37, 52.10 (NCH2), 110.43 (CClBr),
114.95, 117.69 (CHarom), 119.42 (CCl), 129.81 (CNO2), 145.68 (N Carom), 155.93, 157.84
(F Carom), 167.68 (CSN); C24H33BrCl2FN3O2S (MW = 597.41 g/mol) Calcd C:% 48.25,
H:% 5.56, N:% 7.03, S:% 5.36; Found C:% 48.18, H:% 5.31, N:% 7.03, S:% 5.12.
1-(4-Bromo-3,4-dichloro-1-(decylthio)-2-nitrobuta-1,3-dienyl)-4-
(2-fluorophenyl)piperazine (7e)
Followed the typical procedure for 5a. Yield: 120 mg (45.6%); Orange crystal; mp
75–76◦C; Rf (CHCl3): 0.56; IR (KBr, cm−1) = 3050 (C Harom), 2900 (C Haliph), 1580,
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1565 (C C), 1310, 1530 (NO2); UV (CHCl3): λ = 243, 392 nm; H NMR (500 MHz,
CDCl3): ppm = 0.88 (t, 3J = 6.83 Hz, 3H, CH3), 1.27–1.42 (m, 14H, (CH2)7), 1.66–1.72
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(m, 2H, SCH2CH2), 2.98 (t, J = 7.32 Hz, 2H, SCH2), 3.24 (s, 4H, CH2piper), 3.82 (bs,
4H, CH2piper), 6.92–7.10 (m, 4H, C6H4); 13C NMR (125 MHz, CDCl3): ppm = 14.09
(CH3), 22.66, 28.73, 29.05, 29.26, 29.38, 29.47, 29.81, 31.87, 35.56 ((CH2)9), 50.38,