Month 2018
Synthesis of 4-Aroyl-4H-benzo[g]chromenes
2-Amino-4-benzoyl-5,10-dioxo-5,10-dihydro-4H-benzo[g]
chromene-3-carbonitrile (5a). Yield: 91% (81 mg); light
3849, 3742, 3379, 3320, 3203, 3081, 2936, 2843,
2694, 2611, 2550, 248, 2357, 2331, 2268, 2195, 2031,
1915, 1669, 1591, 1514, 1418, 1356, 1254, 1197,
brown solid, mp: 238–240°C (Lit. [30], 233–245); IR:
(KBr) ʋ: 3461, 3340, 3211, 3165, 3073, 2928, 2193,
1991, 1660, 1588, 1402, 1354, 1206, 1047, 947, 853,
1162, 1022, 954, 882, 776, 719, 619, 532 cmÀ1 1H
;
NMR (DMSO-d6, 300 MHz) δ: 3.84 (s, 3H, OMe),
3.90 (s, 3H, OMe), 5.47 (s, 1H, CH), 7.16
(d, J = 8.4 Hz, 1H, ArH), 7.55 (s, 2H, NH2), 7.56 (s,
1H, ArH), 7.88–7.91 (m, 4H, ArH), 8.07–8.10 (m, 1H,
ArH) ppm; 13C NMR (DMSO-d6, 75 MHz) δ: 37.25,
52.36, 55.99, 56.33, 111.44, 111.66, 119.31, 121.84,
126.81, 128.13, 130.88, 131.06, 135.33, 149.13,
150.45, 154.38, 160.39, 177.10, 182.94, 196.22 ppm.
Anal. Calcd for C23H16N2O6: C, 66.34; H, 3.87; N,
6.73. Found: C, 66.11; H, 3.69; N, 6.89.
763, 724, 681, 602, 511 cmÀ1 1H NMR (DMSO-d6,
;
300 MHz) δ: 5.50 (s, 1H, CH), 7.59 (s, 2H, NH2), 7.62
(t, J = 7.5 Hz, 2H, ArH), 7.75 (t, J = 7.5 Hz, 1H, ArH),
7.88 (d, J = 3.0, 3H, ArH), 8.07–8.16 (m, 3H, ArH) ppm;
13C NMR (DMSO-d6, 75 MHz) δ: 37.66, 51.94, 119.10,
121.55, 126.39, 126.85, 129.38, 129.66, 130.90, 131.00,
134.58, 135.04, 135.13, 135.63, 150.45, 160.36, 177.02,
183.00, 198.28 ppm.
2-Amino-4-(4-chlorobenzoyl)-5,10-dioxo-5,10-dihydro-4H-
benzo[g]chromene-3-carbonitrile (5b). Yield: 93% (90 mg);
2-Amino-4-(4-bromobenzoyl)-5,10-dioxo-5,10-dihydro-4H-
benzo[g]chromene-3-carbonitrile (5f). Yield: 82% (89 mg);
light brown solid, mp: 212–213°C; IR (KBr) ʋ: 3439,
3338, 3215, 3073, 2925, 2192, 1665, 1588, 1478, 1406,
dark brown solid, mp: 246–248°C; IR (KBr) ʋ: 3435,
3336, 3211, 3085, 2920, 2642, 2251, 2197, 1664, 1583,
1486, 1366, 1239, 1063, 1001, 840, 792, 727, 601,
1366, 1292, 1207, 1087, 1047, 987, 848, 790, 716 cmÀ1
;
1H NMR (DMSO-d6, 300 MHz) δ: 5.50 (s, 1H, CH),
7.62 (s, 2H, NH2), 7.69 (d, J = 8.4, 2H, ArH), 7.84–7.91
(m, 3H, ArH), 8.07–8.09 (m, 1H, ArH), 8.17 (d, J = 8.4,
2H, ArH) ppm; 13C NMR (DMSO-d6, 75 MHz) δ: 37.73,
51.68, 119.07, 121.24, 126.41, 126.86, 129.58, 130.92,
130.96, 131.54, 134.41, 135.06, 135.34, 139.69, 150.45,
160.32, 176.96, 183.02, 197.47 ppm. Anal. Calcd for
C21H11ClN2O4: C, 64.55; H, 2.84; N, 7.17. Found: C,
1
481 cmÀ1; H NMR (DMSO-d6, 300 MHz) δ: 5.40 (s,
1H, CH), 7.56 (bs, 2H, ArH), 7.65 (s, 2H, NH2), 7.78–
7.80 (m, 2H, ArH), 7.87 (bs, 5H, ArH), 8.04 (bs, 1H,
ArH); 13C NMR (DMSO-d6, 75 MHz) δ: 51.66, 114.10,
114.36, 119.08, 121.23, 127.71, 130.15, 130.71, 130.95,
132.05, 132.86, 134.43, 134.72, 160. 31, 176.96,
194.27, 197.69 ppm. Anal. Calcd for C21H11BrN2O4:
C, 57.95; H, 2.55; N, 6.44. Found: C, 58.08; H, 2.47;
N, 6.32.
64.74; H, 2.70; N, 7.02.
2-Amino-4-(4-methylbenzoyl)-5,10-dioxo-5,10-dihydro-4H-
benzo[g]chromene-3-carbonitrile (5c). Yield: 90% (83 mg);
2-Amino-4-(4-hydroxybenzoyl)-5,10-dioxo-5,10-dihydro-4H-
benzo[g]chromene-3-carbonitrile (5g). Yield: 84% (78 mg);
dark brown solid, mp 260–261°C; IR (KBr) ʋ: 3462, 3332,
light brown solid, mp: 215–217°C; IR (KBr) ʋ: 3468,
3343, 3204, 3168, 3039, 2921, 2363, 2194, 1662, 1593,
1402, 1357, 1299, 1241, 1202, 1044, 949, 842, 787, 723,
3276, 2193, 1661, 1588, 1360, 1298, 1216, 1042, 952,
1
595, 507 cmÀ1; H NMR (DMSO-d6, 300 MHz) δ: 2.43
849, 798, 723, 601, 523 cmÀ1 1H NMR (DMSO-d6,
;
(s, 3H, CH3), 5.45 (s, 1H, CH), 7.41 (d, J = 7.8 Hz, 2H,
ArH), 7.56 (s, 2H, NH2) 7.88–7.90 (m, 3H, ArH), 8.03–
8.06 (m, 3H, ArH) ppm; 13C NMR (DMSO-d6, 75 MHz)
δ: 21.72, 37.49, 52.09, 121.65, 126.38, 129.95, 130.89,
131.02, 135.02, 135.25, 145.20, 170.55, 171.10, 183.00,
197.64 ppm. Anal. Calcd for C22H14N2O4: C, 71.35; H,
3.81; N, 7.56. Found: C, 71.64; H, 3.68; N, 7.67.
2-Amino-4-(4-methoxybenzoyl)-5,10-dioxo-5,10-dihydro-4H-
benzo[g]chromene-3-carbonitrile (5d). Yield: 85% (82 mg);
300 MHz) δ: 5.38 (s, 1H, CH), 6.92 (d, J = 6.9 Hz, 2H,
ArH), 7.51 (s, 2H, NH2), 7.89 (s, 3H, ArH), 8.01–8.06 (t,
J = 8.0, 3H, ArH), 10.57 (s, 1H, OH) ppm; 13C NMR
(DMSO-d6, 75 MHz) δ: 37.11, 52.42, 115.95,
119.20,121.86, 126.88, 130.86, 131.05, 132.47, 150.42,
160.31, 163.44, 177.08, 182.96, 196.00 ppm. Anal. Calcd
for C21H12N2O5: C, 67.74; H, 3.25; N, 7.52. Found: C,
67.91; H, 3.08; N, 7.41.
2-Amino-4-(4-fluorobenzoyl)-5,10-dioxo-5,10-dihydro-4H-
benzo[g]chromene-3-carbonitrile (5h). Yield: 95% (88 mg);
light brown solid, mp: 236–239°C (Lit. [30], 234–236); IR:
(KBr) ʋ: 3328, 3185, 2979, 2944, 2845, 2623, 2200, 1667,
1590, 1514, 1415, 1320, 1237, 1176, 1025, 958, 842, 785,
red solid, mp: 236–237°C (Lit. [30], 254–256); IR (KBr) ʋ:
3463, 3333, 3206, 3168, 3079, 2193, 1664, 1589, 1509,
1403, 1358, 1302, 1208, 1043, 951, 851, 796, 721, 589,
1
719, 588, 528 cmÀ1; H NMR (DMSO-d6, 300 MHz) δ:
3.89 (s, 3H, CH3), 5.44 (s, 1H, CH), 7.12 (d, J = 8.7 Hz,
2H, ArH), 7.54 (s, 2H, NH2), 7.87–7.90 (m, 3H, ArH),
8.07–8.14 (m, 3H, ArH) ppm; 13C NMR (DMSO-d6,
75 MHz) δ: 37.28, 52.29, 56.15, 114.64, 121.75, 126.37,
126.83, 128.32, 130.87, 131.03, 132.18, 135.01, 135.34,
1
510 cmÀ1; H NMR (DMSO-d6, 300 MHz) δ: 5.51 (s,
1H, CH), 7.45 (t, J = 7.4 Hz, 2H, ArH), 7.60 (s, 2H,
NH2), 7.87–7.94 (m, 3H, ArH), 8.09 (t, J = 7.5 Hz, 1H,
ArH), 8.26 (t, J = 8.7 Hz, 2H, ArH) ppm; 13C NMR
(DMSO-d6, 75 MHz) δ: 37.67, 51.81, 116.36, 116.65,
119.09, 121.34, 126.39, 126.86, 130.91, 130.98, 132.43,
132.76, 132.87, 135.05, 135.33, 150.44, 160.33, 162.33,
176.99, 183.01, 196.97 ppm.
162.33, 164.41, 177.12, 182.99, 196.47 ppm.
2-Amino-4-(3,4-dimethoxybenzoyl)-5,10-dioxo-5,10-dihydro-
4H-benzo[g]chromene-3-carbonitrile (5e).
Yield: 84%
(87 mg); light brown solid, mp: 219–220°C; IR (KBr) ʋ:
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet