N. O. Mahmoodi et al.
2-(3,4-Dihydronaphthalen-1(2H)-ylidene)-N-phenylhydrazine-1-
carboxamide 1a
White solid, yield: 98 %, m.p. 208–210 °C, FT-IR (KBr, m cm-1): 3359, 3201
(stretch N–H), 3109 (stretch C–H Ar.), 2934 (stretch C–H ali.), 1684 (stretch C=O,
amide), 1597, 1528 (stretch C=C), 1442 (bending CH2), 1299, 1129 (stretch C–N),
1
751, 622 (OOP. C–H). H NMR (400 MHz, DMSO-d6): d; 9.72 (s, 1H, NH, He),
8.89 (s, 1H, NH, Hd), 8.29 (d, J = 6.8 Hz, 1H, Hl), 7.64 (d, J = 7.6 Hz, 2H, Hc),
7.32–7.19 (m, 5H, Hb, Hi, Hj, Hk), 7.02 (t, J = 7 Hz, 1H, Ha), 2.74 (s, 2H, Hh), 2.63
(s, 2H, Hf), 1.84 (s, 2H, Hg) ppm. 13C NMR (100 MHz, DMSO-d6): d;. 13C NMR
(100 MHz, DMSO-d6): d; 158.1 (C=O), 142.7 (C=N), 139.0, 138.9, 130.1, 128.0,
128.4, 126.9, 125.7, 122.4, 121.7, 119.5, 119.4 (10 C), 28.0 (Cg), 26.9 (Cf) ppm.
2-(2,3-Dihydronaphthalen-1H-inden-1-ylidene)-N-phenylhydrazine-1-
carboxamide 1b
White solid, yield: 98 %, m.p. 222–224 °C, FT-IR (KBr, m cm-1): 3362, 3193
(stretch N–H), 3085 (stretch C–H Ar.), 2914 (stretch C–H ali.), 1681 (stretch C=O,
amide), 1597, 1537 (stretch C=C), 1442 (bending CH2), 1313, 1127 (stretch C–N),
1
750, 688, 619 (OOP. C–H). H NMR (400 MHz, DMSO-d6): d; 9.69 (s, 1H, NH,
He), 8.91 (s, 1H, NH, Hd), 7.97 (d, J = 7.6 Hz, 1H, Hk), 7.67 (d, J = 8.2, 1.2 Hz,
2H, Hc), 7.38–7.28 (m, 5H, Hb, Hj, Hi, Hh), 7.01 (t, J = 7.4 Hz, 1H, Ha), 3.08 (t,
J = 6.4 Hz, 2H, Hg), 2.82–2.79 (m, 2H, Hf) ppm. 13C NMR (100 MHz, DMSO-d6):
d; 155.1 (C=O), 147.9 (C=N), 139.0, 137.8, 129.9, 128.4, 126.7, 125.5, 122.2,
121.7, 119.4, 119.3 (10 C), 28.0 (Cg), 26.9 (Cf) ppm.
2-Cyclohexylidene-N-phenylhydrazine-1-carboxamide 1c
White solid, yield: 98 %, m.p. 207–208 °C, FT-IR (KBr, m cm-1): 3289, 3135
(stretch N–H), 3086 (stretch C–H Ar.), 2934, 2859 (stretch C–H ali.), 1656 (stretch
C=O, amide), 1601, 1550, 1499 (stretch C=C), 1442 (bending CH2), 1309, 1213
1
(stretch C–N), 758, 642 (OOP. C–H). H NMR (400 MHz, DMSO-d6): d; 9.60 (s,
1H, NH, He), 8.73 (s, 1H, NH, Hd), 7.64 (d, J = 7.6 Hz, 2H, Hc), 7.32 (d,
J = 7.8 Hz, 2H, Hb), 7.03 (t, J = 7.2 Hz, 1H, Ha), 2.42 (s, 2 h, Hf or Hf’), 2.35 (t,
J = 7.4 Hz, 2H, Hf’ or Hf), 1.70 (s, 2H, Hh), 1.62 (m, 4H, Hg) ppm. 13C NMR
(100 MHz, DMSO-d6): d; 153.6 (C=N), 139.2 (C=O), 139.1, 128.4, 122.0, 119.0,
118.9, 34.7, 26.8, 26.5, 25.5, 25.1 ppm.
2-Cyclopentylidene-N-phenylhydrazine-1-carboxamide 1d
White solid, yield: 98 %, m.p. 178–180 °C, FT-IR (KBr, m cm-1): 3348, 3193
(stretch N–H), 3082 (stretch C–H Ar.), 2961, 2874 (stretch C–H ali.), 1677 (stretch
C=O, amide), 1600, 1532 (stretch C=C), 1443 (bending CH2), 1188 (stretch C–N),
1
751, 612 (OOP. C–H). H NMR (400 MHz, DMSO-d6): d; 9.23 (s, 1H, NH, He),
8.65 (s, 1H, NH, Hd), 7.57 (d, J = 7.6 Hz, 2H, Hc), 7.25 (t, J = 8.0 Hz, 2H, Hb),
6.97 (t, J = 7.4 Hz, 1H, Ha), 2.37 (t, J = 7.2 Hz, 2H, Hf or Hi), 2.28 (t, J = 7.2 Hz,
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