BAKHERAD ET AL.
7
3.4.3
| 1-([1-Butyl-1H-1,2,3-triazol-4-yl]methyl)-2-phenyl-1H-
132.1, 133.5, 136.8, 142.5, 150.2, 185.8; MS (m/z):
436 (M)+; Anal. calcd for C22H21BrN4O: C, 60.42; H,
4.84; N, 12.81%; Found: C, 60.60; H, 4.94; N, 12.97%.
indole-3-carbaldehyde (5c)
IR (KBr): 3,077 (w), 2,945 (m), 2,380 (m), 1,652 (s), 1,535
(m), 1,459 (m), 1,420 (w) cm−1 1H NMR (300 MHz,
;
3.4.7
| 1-([1-Benzyl-1H-1,2,3-triazol-4-yl]methyl)-
DMSO-d6) δ: 0.77 (t, 3h, j = 7.2 Hz, CH3), 1.02–1.09 (m,
2H, CH2), 1.58–1.68 (m, 2H, ch2), 4.20 (t, 2H, J = 7.2 Hz,
CH2), 5.31 (s, 2H, CH2), 7.23–7.28 (m, 2H, Ar-H),
7.54–7.61 (m, 4H, Ar-H), 7.66–7.69 (m, 2H, Ar-H), 7.89 (s,
2-(4-chlorophenyl)-1H-indole-3-carbaldehyde (5g)
IR (KBr): 3,078 (w), 2,961 (m), 2,387 (m), 1,655 (s), 1,536
(m), 1,461 (m), 1,410 (w) cm−1 1H NMR (300 MHz,
;
1H, C-H), 8.13–8.16 (m, 1H, Ar-H), 9.53 (s, 1H, CHO). 13
C
DMSO-d6) δ: 5.43 (s, 2H, CH2), 5.55 (s, 2H, CH2),
7.23–7.25 (m, 2H, Ar-H), 7.25–7.38 (m, 5H, Ar-H), 7.66 (d,
2H, J = 8.1 Hz, Ar-H), 7.71–7.74 (m, 1H, Ar-H), 7.77 (d,
2H, J = 8.4 Hz, Ar-H), 8.08 (s, 1H, C-H), 8.23–8.26 (m,
1H, Ar-H), 9.62 (s, 1H, CHO). 13C NMR (75 MHz, DMSO-
d6) δ: 53.2, 112.0, 115.7, 121.4, 123.6, 124.1, 124.4, 125.1,
127.3, 128.5, 129.1, 129.2, 133.3, 135.5, 136.3, 136.8,
142.9150.1, 185.8; MS (m/z): 426 (M)+; Anal.calcd for
C25H19CLN4O: C, 70.34; H, 4.49; N, 13.12%; Found: C,
70.51; H, 4.58; N, 13.27%.
NMR (75 MHz, DMSO-d6) δ: 13.7, 19.4, 34.1, 49.5, 111.7,
115.5, 121.5, 123.7, 124.6, 125.1, 128.0, 129.1, 129.3,
130.6, 131.2, 131.5, 136.4, 150.9, 186.0; MS (m/z):
358 (M)+; Anal. calcd for C22H22N4O: C, 73.72; H, 6.19; N,
15.63%; Found: C, 73.90; H, 6.30; N, 15.80%.
3.4.4
| 1-([1-Benzyl-1H-1,2,3-triazol-4-yl]methyl)-
2-(4-bromophenyl)-1H-indole-3-carbaldehyde (5d)
IR (KBr): 3,069 (w), 2,960 (m), 2,382 (m), 1,650 (s), 1,530
(m), 1,460 (m), 1,417 (w) cm−1 1H NMR (300 MHz,
;
3.4.8
| 1-((1-[4-Chlorobenzyl]-1H-1,2,3-triazol-4-yl)methyl)-
DMSO-d6) δ: 5.43 (s, 2H, CH2), 5.55 (s, 2H, CH2),
7.23–7.25 (m, 2H, Ar-H), 7.30–7.41 (m, 5H, Ar-H),
7.68–7.74 (m, 3H, Ar-H), 7.78–7.81 (m, 2H, Ar-H), 8.08 (s,
2-(4-chlorophenyl)-1H-indole-3-carbaldehyde (5h)
IR (KBr): 3,076 (w), 2,946 (m), 2,383 (m), 1,652 (s), 1,533
(m), 1,460 (m), 1,416 (w) cm−1 1H NMR (300 MHz,
;
1H, C-H), 8.23–8.26 (m, 1H, Ar-H), 9.62 (s, 1H, CHO). 13
C
DMSO-d6) δ: 5.43 (s, 2H, CH2), 5.55 (s, 2H, CH2),
7.25–7.33 (m, 2H, Ar-H), 7.33–7.38 (m, 2H, Ar-H),
7.41–7.53 (m, 2H, Ar-H), 7.64–7.67 (m, 2H, Ar-H),
7.71–7.74 (m, 1H, Ar-H), 7.75–7.78 (m, 2H, Ar-H), 8.06 (s,
NMR (75 MHz, DMSO-d6) δ: 53.2, 112.0, 115.6, 121.4,
123.6, 124.1, 124.3, 124.4, 125.1, 127.7, 128.2, 128.5,
129.1, 132.1, 133.5, 136.3, 136.8, 142.9, 150.1, 185.8; MS
(m/z): 470 (M)+; Anal. calcd for C25H19BrN4O: C, 63.70; H,
4.06; N, 11.89%; Found: C, 63.53; H, 4.15; N, 11.74%.
1H, C-H), 8.22–8.25 (m, 1H, Ar-H), 9.62 (s, 1H, CHO). 13
C
NMR (75 MHz, DMSO-d6) δ: 52.4, 112.0, 115.7, 121.4,
123.5, 124.1, 124.4, 125.1, 127.3, 129.2, 130.2, 130.7,
133.3, 135.3, 135.5, 136.8, 143.0, 150.1, 185.8; MS (m/z):
460 (M)+; Anal. calcd for C25H18Cl2N4O: C, 65.09; H,
3.93; N, 12.14%; Found: C, 65.26; H, 3.85; N, 12.29%.
3.4.5
| 2-(4-Bromophenyl)-1-((1-[4-chlorobenzyl]-1H-
1,2,3-triazol-4-yl)methyl)-1H-indole-3-carbaldehyde (5e)
IR (KBr): 3,073 (w), 2,951 (m), 2,385 (m), 1,649 (s), 1,525
(m), 1,458 (m), 1,418 (w) cm−1 1H NMR (300 MHz,
;
DMSO-d6) δ: 5.43 (s, 2H, CH2), 5.55 (s, 2H, CH2),
7.25–7.28 (m, 2H, Ar-H), 7.32–7.38 (m, 3H, Ar-H),
7.43–7.49 (m, 2H, Ar-H), 7.68–7.73 (m, 3H, Ar-H),
7.78–7.88 (m, 2H, Ar-H), 8.07 (s, 1H, C-H), 8.23–8.25 (m,
1H, Ar-H), 9.62 (s, 1H, CHO). 13C NMR (75 MHz, DMSO-
d6) δ: 52.4, 112.0, 115.7, 121.4, 123.6, 124.1, 124.3, 124.4,
125.1, 127.7, 129.2, 130.2, 132.1, 132.3, 133.3, 133.5,
135.3, 136.8, 143.0, 150.1, 185.8; MS (m/z): 503 (M)+;
Anal. calcd for C25H18BrClN4O: C, 59.37; H, 3.59; N,
11.08%; Found: C, 59.55; H, 3.67; N, 11.25%.
3.4.9
| 1-([1-Butyl-1H-1,2,3-triazol-4-yl]methyl)-
2-(4-chlorophenyl)-1H-indole-3-carbaldehyde (5i)
IR (KBr): 3,073 (w), 1,939 (m), 2,375 (m), 1,657 (s), 1,532
(m), 1,455 (m), 1,428 (w) cm−1 1H NMR (300 MHz,
;
DMSO-d6) δ: 0.86 (t, 3H, J = 7.2 Hz, ch3), 1.11–1.23 (m,
2H, CH2), 1.67–1.77 (m, 2H, CH2), 4.29 (t, 2H, J = 6.9 Hz,
CH2), 5.41 (s, 2H, CH2), 7.32–7.38 (m, 2H, Ar-H),
7.68–7.72 (m, 2H, Ar-H), 7.72–7.75 (m, 1H, Ar-H),
7.78–7.82 (m, 2H, Ar-H), 8.02 (s, 1H, C-H), 8.22–8.27 (m,
1H, Ar-H), 9.62 (s, 1H, CHO). 13C NMR (75 MHz, DMSO-
d6) δ: 13.7, 19.4, 32.0, 49.5, 112.0, 115.6, 121.4, 121.5,
123.5, 123.8, 124.4, 125.1, 127.3, 129.2, 129.4, 133.1,
133.3, 135.5, 136.8, 142.5, 150.1, 185.8; MS (m/z):
392 (M)+; Anal. calcd for C22H21ClN4O: C, 67.26; H,
5.39; N, 14.26%; found: C, 67.07; H, 5.29; N, 14.42%.
3.4.6
| 2-(4-Bromophenyl)-1-([1-butyl-1H-1,2,3-triazol-4-yl]
methyl)-1H-indole-3-carbaldehyde (5f)
IR(KBr): 3,080 (w), 2,940 (m), 2,371 (m), 1,651 (s), 1,520
(m), 1,460 (m), 1,419 (w) cm−1 1H NMR (300 MHz,
;
DMSO-d6) δ: 0.86 (t, 3H, J = 7.2 Hz, CH3), 1.11–1.21 (m,
2H, CH2), 1.67–1.77 (m, 2H, CH2), 4.29 (t, 2H, J = 7.2 Hz,
CH2), 5.41 (s, 2H, CH2), 7.30–7.38 (m, 2H, Ar-H),
7.70–7.76 (m, 3H, Ar-H), 7.82–7.85 (m, 2H, Ar-H), 8.02 (s,
3.4.10
| 1-([1-Benzyl-1H-1,2,3-triazol-4-yl]methyl)-2-(p-tolyl)-
1H-indole-3-carbaldehyde (5j)
1H, C-H), 8.22–8.25 (m, 1H, Ar-H), 9.62 (s, 1H, CHO). 13
C
IR (KBr): 3,079 (w), 2,937 (m), 2,380 (m), 1,653 (s), 1,531
NMR (75 MHz, DMSO) δ: 13.7, 19.4, 32.0, 49.5, 112.0,
(m), 1,469 (m), 1,427 (w) cm−1 1H NMR (300 MHz,
;
115.6, 121.4, 123.5, 123.8, 124.3, 124.5, 125.1, 127.7,
DMSO-d6) δ: 2.43 (s, 3H, CH3), 5.41 (s, 2H, CH2), 5.54 (s,