3968
N. M. A. El-Rahman et al.
2-Amino-4-(4-hydroxyphenyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-
chromene-3-carbonitrile (5 k): Mp 205–2078C. IR (KBr) vmax/cm21: 3650
1
(OH), 3325,3100 (NH2), 2195 (C N), 1679 (C55O); H NMR (300 MHz,
;;
CDCL3): d ¼ 1.05 (s, 3H, CH3), 1.14 (s, 3H, CH3), 2.12 (d, 1H,
JAB ¼ 16 Hz, H-8a), 2.23 (d, 1H, JAB ¼ 16 Hz, H-8b), 2.44 (s, 2H, C6-H),
4.33 (s, 1H, C4-H), 5.59 (s, 2H, NH2, D2O exchangeable), 7.01–7.33 (m, 4H,
Ar-H), 8.1 (br s, 1H, OH, D2O exchangeable).
2-Amino-4-(3-hydroxy-4-methoxphenyl)-5,6,7,8-tetrahydro-7,7-dimethyl
-5-oxo-4H-chromene-3-carbonitrile (5l): Mp 229–2318C. IR (KBr) vmax
/
cm21: 3440 (OH), 3310, 3172 (NH2), 2240 (C N), 1680 (C55O); 1H
NMR (300 MHz, CDCL3): d ¼ 1.05 (s, 3H, CH3), 1.20 (s, 3H, CH3), 2.22
(d, 1H, JAB ¼ 16 Hz, H-8a), 2.32 (d, 1H, JAB ¼ 16 Hz, H-8b), 2.50 (s, 2H,
C6-H), 3.75 (s, 3H, OCH3), 4.52 (s, 1H, C4-H), 5.15 (s, 2H, NH2, D2O
exchangeable), 7.21–7.42 (m, 4H, Ar-H), 7.61 (br s, 1H, OH, D2O
exchangeable).
;;
2-Amino-4-(naphthalen-2-yl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-
chromene-3-carbonitrile (5 m): Mp 248–2508C. IR (KBr) vmax/cm21
:
3379, 3170 (NH2), 2236 (C N), 1678 (C55O); 1H NMR (300 MHz,
DMSO- d6): d ¼ 0.96 (s, 3H, CH3), 1.05 (s, 3H, CH3), 2.15 (d, 1H,
JAB ¼ 16 Hz, H-8a), 2.29 (d, 1H, JAB ¼ 16 Hz, H-8b), 2.55 (s, 2H, C6-H),
4.34 (s, 1H, C4-H), 5.51 (s, 2H, NH2, D2O exchangeable), 6.99–7.39
(m, 7H, Ar-H). MS (m/z): 344 (Mþ). Calcd. for C22H20N2O2 (344.41): C,
76.72; H, 5.85; N, 8.13%. Found: C, 76.90; H, 5.80; N, 8.00%.
;;
2-Amino-4-(benzo[d][1,3]dioxol-5-yl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-
oxo-4H-chromene-3-carbonitrile (5n): Mp 210–2128C. IR (KBr) vmax
/
cm21: 3388, 3179 (NH2), 2240 (C N), 1675 (C55O); H NMR (300 MHz,
DMSO-d6): d ¼ 1.06 (s, 3H, CH3), 1.12 (s, 3H, CH3), 2.12 (d, 1H,
JAB ¼ 16 Hz, H-8a), 2.27 (d, 1H, JAB ¼ 16 Hz, H-8b), 2.49 (s, 2H, C6-H),
4.33 (s, 1H, C4-H), 4.59 (s, 2H, NH2, D2O exchangeable), 5.91 (s, 2H,
CH2) 6.69–6.74 (m, 3H, Ar-H); 13C NMR (DMSO-d6), d ¼ 195.65 (CO),
162.32 (C-8a), 158.47 (C-2), 147.23, 145.89, 138.89, 120.34 (4C), 119.70
(CN), 112.84 (C-4a), 108.01, 107.58 (2C), 100.91 (1C)., 58.61 (C-3), 50.11
(C-6), 39.9 (C-8), 35.30 (C-4), 31.8 (C-7), 28.35, 27.00. MS (m/z): 338
(Mþ). Calcd. for C19H18N2O4 (338.36): C, 67.44; H, 5.36; N, 8.28%.
Found: C, 67.30; H, 5.40; N, 8.38%.
1
;;
2-Amino-4-(fur-2-yl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromen
e-3-carbonitrile (5o): Mp 198–2008C. IR (KBr) vmax/cm21: 3374, 3146
(NH2), 2235 (C N), 1679 (C55O); 1H NMR (300 MHz, CDCL3):
;;
d ¼ 1.06 (s, 3H, CH3), 1.13 (s, 3H, CH3), 2.17 (d, 1H, JAB ¼ 16 Hz, H-8a),
2.29 (d, 1H, JAB ¼ 16 Hz, H-8b), 2.46 (s, 2H, C6-H), 4.58 (s, 1H, C4-H),
4.79 (s, 2H, NH2, D2O exchangeable), 6.18–7.27 (m, 3H, furyl-H); 13C