Open Access Article
This Open Access Article is licensed under a Creative Commons Attribution 3.0 Unported Licence
DOI: 10.1039/C5RA90037A
(Correction)
RSC Adv., 2015, 5, 34910-34912
Correction: Sustainable construction: admicellar catalysed synthesis of pyrimido[4,5-b]quinolines in an aqueous system
I. R.
Siddiqui
*a,
Pragati
Rai
a,
Rahila
a,
Hoezyfa
Sagir
a and
Prashant
Singh
b
aLaboratory of Green Synthesis, Department of Chemistry, University of Allahabad, Allahabad-211002, India. E-mail: dr.irsiddiqui@gmail.com
bNanotechnology Application Centre, University of Allahabad, Allahabad, 211002, India
Received
7th April 2015
, Accepted 7th April 2015
First published on 15th April 2015
Abstract
Correction for ‘Sustainable construction: admicellar catalysed synthesis of pyrimido[4,5-b]quinolines in an aqueous system' by I. R. Siddiqui et al., RSC Adv., 2015, 5, 27603–27609.
The characterization data of compounds 4a–4l in the Experimental section of the paper is incorrect. The correct characterization data is given below. (Part of this data was previously available as electronic supplementary information (ESI). No additional ESI exists for this work.)
5-(4-Chlorophenyl)benzo[G]pyrimido[4,5-b]quinoline-2,4,6,11(1h,3h,5h,12h)-tetraone (4a)
Orange powder; mp 294 °C. IR (KBr) (νmax/cm−1): 3315, 3244, 1726, 1651, 1596, 1543. 1H NMR (400 MHz, DMSO-d6): δH (ppm) 5.09 (s, 1H, CH), 7.28 (d, JHH = 8.4 Hz, 2H), 7.37 (d, JHH = 8.5 Hz, 2H), 7.77–8.04 (m, 4H, H-Ar), 9.39 (s, 1H, NH), 10.22 (s, 1H, NH), 10.95 (s, 1H, NH). 13C NMR (100 MHz, DMSO-d6): δC (ppm) 35.0, 90.1, 118.9, 126.8, 126.9, 128.7, 130.8, 131.5, 132.6, 132.9, 134.3, 135.8, 139.6, 144.5, 148.7, 151.2, 164.4, 179.8, 182.5. MS (EI, 70 eV): m/z (%): 405 (M+, 10), 371 (10), 325 (45), 234 (28), 156 (26), 77 (78), 57 (80), 43 (100). For C21H12ClN3O4 (405.79): C, 62.16; H, 2.98; N, 10.36; found: C, 62.25; H, 2.85; N, 10.49.5-(4-Bromophenyl)benzo[G]pyrimido[4,5-b]quinoline-2,4,6,11(1h,3h,5h,12h)-tetraone (4b)
Orange powder; mp 299 °C. IR (KBr) (νmax/cm−1): 3406, 3249, 3054, 1735, 1661, 1605, 1577. 1H NMR (400 MHz, DMSO-d6): δH (ppm) 5.14 (s, 1H, CH), 6.91–7.99 (m, 8H, H-Ar), 9.34 (s, 1H, NH), 10.18 (s, 1H, NH), 10.86 (s, 1H, NH). 13C NMR (100 MHz, DMSO-d6): δC (ppm) 36.7, 87.9, 119.8, 125.4, 126.8, 126.9, 129.9, 131.6, 132.3, 134.7, 135.9, 138.8, 149.1, 154.8, 159.3, 163.9, 181.4, 184.7. MS (EI, 70 eV): m/z (%): 449 (M+, 8), 371 (12), 373 (50), 278 (30), 156 (22), 76 (80), 57 (80), 43 (100). For C21H12BrN3O4 (450.24): C, 56.02; H, 2.69; N, 9.33; found: C, 56.19; H, 2.57; N, 14.34.5-(4-Nitrophenyl)benzo[G]pyrimido[4,5-b]quinoline-2,4,6,11(1h,3h,5h,12h)-tetraone (4c)
Red powder; mp 297 °C. IR (KBr) (νmax/cm−1): 3358, 3240, 3073, 1719, 1684, 1631, 1577. 1H NMR (400 MHz, DMSO-d6): δH (ppm) 5.25 (s, 1H, CH), 7.36 (d, JHH = 8.5 Hz, 2H), 7.48 (d, JHH = 8.5 Hz, 2H), 7.73–8.14 (m, 4H, H-Ar), 9.31 (s, 1H, NH), 10.20 (s, 1H, NH), 10.83 (s, 1H, NH). 13C NMR (100 MHz, DMSO-d6): δC (ppm) 37.2, 88.0, 119.3, 126.8, 126.9, 128.7, 131.0, 131.2, 132.1, 132.8, 134.7, 136.2, 138.9, 145.0, 151.3, 160.1, 163.5, 181.8, 183.6. MS (EI, 70 eV): m/z (%): 416 (M+, 15), 371 (16), 340 (54), 245 (34), 156 (18), 76 (84), 57 (76), 43 (100). For C21H12N4O6 (416.34): C, 60.58; H, 2.91; N, 13.46; found: C, 60.72; H, 2.85; N, 13.51.5-Phenylbenzo[G]pyrimido[4,5-b]quinoline-2,4,6,11(1h,3h,5h,12h)-tetraone (4d)
Red powder; mp 300 °C. IR (KBr) (νmax/cm−1): 3411, 3250, 3065, 1717, 1645, 1608, 1561. 1H NMR (400 MHz, DMSO-d6): δH (ppm) 5.22 (s, 1H, CH), 7.11–8.11 (m, 9H, H-Ar), 9.29 (s, 1H, NH), 10.11 (s, 1H, NH), 10.82 (s, 1H, NH). 13C NMR (100 MHz, DMSO-d6): δC (ppm) 35.6, 86.7, 119.6, 124.4, 126.6, 126.8, 127.9, 128.9, 131.6, 132.4, 134.4, 135.7, 139.8, 151.2, 155.7, 159.3, 163.4, 181.8, 185.6. MS (EI, 70 eV): m/z (%): 371 (M+, 5), 328 (12), 295 (42), 200 (30), 156 (22), 76 (80), 43 (100). For C21H13N3O4 (371.35): C, 67.92; H, 3.53; N, 11.32; found: C, 68.06; H, 3.51; N, 11.46.5-m-Tolylbenzo[G]pyrimido[4,5-b]quinoline-2,4,6,11(1h,3h,5h,12h)-tetraone (4e)
Red powder; mp 282 °C. IR (KBr) (νmax/cm−1): 3327, 3268, 3050, 1723, 1657, 1610, 1529. 1H NMR (400 MHz, DMSO-d6): δH (ppm) 2.71 (s, 3H, Me), 5.25 (s, 1H, CH), 7.03–8.15 (m, 8H, H-Ar), 9.24 (s, 1H, NH), 10.16 (s, 1H, NH), 10.89 (s, 1H, NH). 13C NMR (100 MHz, DMSO-d6): δC (ppm) 24.5, 35.5, 86.6, 117.6, 124.0, 126.4, 127.0, 127.4, 128.0, 128.7, 131.4, 132.5, 134.1, 135.4, 135.7, 138.1, 139.9, 152.5, 161.2, 163.3, 182.9, 183.8. MS (EI, 70 eV): m/z (%): 385 (M+, 8), 294 (40), 214 (22), 156 (28), 91 (70), 57 (78), 43 (100). For C22H15N3O4 (385.37): C, 68.57; H, 3.92; N, 10.90; found: C, 68.71; H, 3.86; N, 10.85.5-o-Tolylbenzo[G]pyrimido[4,5-b]quinoline-2,4,6,11(1h,3h,5h,12h)-tetraone (4f)
Red powder; mp 277 °C. IR (KBr) (νmax/cm−1): 3417, 3248, 3055, 1714, 1657, 1609, 1533. 1H NMR (400 MHz, DMSO-d6): δH (ppm) 2.77 (s, 3H, Me), 5.17 (s, 1H, CH), 7.01–8.04 (m, 8H, H-Ar), 9.31 (s, 1H, NH), 10.17 (s, 1H, NH), 10.87 (s, 1H, NH). 13C NMR (100 MHz, DMSO-d6): δC (ppm) 22.2, 35.6, 86.8, 117.1, 124.0, 126.3, 126.9, 127.5, 127.9, 128.7, 131.3, 132.6, 134.2, 135.3, 135.4, 138.0, 139.1, 151.2, 158.1, 163.8, 182.4, 183.3. MS (EI, 70 eV): m/z (%): 385 (M+, 10), 309 (44), 214 (26), 156 (20), 91 (74), 57 (82), 43 (100). For C22H15N3O4 (385.37): C, 68.57; H, 3.92; N, 10.90; O, 16.61; found: C, 68.80; H, 3.76; N, 10.92.5-p-Tolylbenzo[G]pyrimido[4,5-b]quinoline-2,4,6,11(1h,3h,5h,12h)-tetraone (4g)
Red powder; mp 311 °C. IR (KBr) (νmax/cm−1): 3408, 3253, 3059, 1717, 1656, 1608, 1517. 1H NMR (400 MHz, DMSO-d6): δH (ppm) 2.19 (s, 3H, Me), 5.07 (s, 1H, CH), 7.02 (d, JHH = 7.7 Hz, 2H), 7.19 (d, JHH = 7.7 Hz, 2H), 7.79–8.04 (m, 4H, H-Ar), 9.21 (s, 1H, NH), 10.14 (s, 1H, NH), 10.89 (s, 1H, NH). 13C NMR (100 MHz, DMSO-d6): δC (ppm) 21.2, 35.4, 86.5, 114.6, 126.5, 126.8, 129.2, 130.5, 130.9, 131.4, 132.5, 134.4, 135.8, 138.7, 144.5, 148.8, 159.1, 163.4, 179.9, 183.2. MS (EI, 70 eV): m/z (%): 385 (M+, 5), 294 (45), 214 (30), 156 (20), 76 (78), 57 (82), 43 (100). For C22H15N3O4 (385.37): C, 68.57; H, 3.92; N, 10.90; found: C, 68.51; H, 3.86; N, 10.80.5-(4-Methoxyphenyl)benzo[G]pyrimido[4,5-b]quinoline-2,4,6,11(1h,3h,5h,12h)-tetraone (4h)
Orange powder; mp 301 °C. IR (KBr) (νmax/cm−1): 3423, 3178, 3057, 1704, 1681, 1611, 1533. 1H NMR (400 MHz, DMSO-d6): δH (ppm) 3.64 (s, 3H, OMe), 5.03 (s, 1H, CH), 6.76 (d, JHH = 7.7 Hz, 2H, H-Ar), 7.21 (d, JHH = 7.6 Hz, 2H, H-Ar), 7.81–8.02 (m, 4H, H-Ar), 9.32 (s, 1H, NH), 10.16 (s, 1H, NH), 10.91 (s, 1H, NH). 13C NMR (100 MHz, DMSO-d6): δC (ppm) 32.5, 56.7, 86.5, 114.9, 124.5, 126.2, 126.9, 129.7, 130.0, 130.5, 133.9, 133.1, 133.7, 135.4, 138.0, 144.7, 159.1, 163.6, 179.7, 183.1. MS (EI, 70 eV): m/z (%): 401 (M+, 15), 358 (14), 325 (30), 230 (26), 156 (22), 57 (76), 43 (100). For C22H15N3O5 (401.37): C, 65.83; H, 3.77; N, 10.47; found: C, 65.88; H, 3.74; N, 10.58.5-(4-Chlorophenyl)-1,3-dimethylbenzo[G]pyrimido[4,5-b]quinoline-2,4,6,11(1h,3h,5h,12h)-tetraone (4i)
Orange powder; mp 251 °C. IR (KBr) (νmax/cm−1): 3402, 1716, 1654, 1580, 1517. 1H NMR (400 MHz, DMSO-d6): δH (ppm) 3.19 (s, 3H, NMe), 3.36 (s, 3H, NMe), 5.66 (s, 1H, CH), 7.10–7.88 (m, 8H, H-Ar), 13.11 (s, 1H, NH). 13C NMR (100 MHz, DMSO-d6): δC (ppm) 29.7, 31.4, 35.3, 86.2, 118.9, 124.0, 126.8, 126.9, 130.4, 131.2, 131.6, 132.6, 134.4, 135.1, 138.9, 150.1, 155.1, 156.4, 164.1, 181.6, 186.9. MS (EI, 70 eV): m/z (%): 433 (M+, 5), 322 (8), 271 (30), 235 (100), 156 (72), 76 (82), 57 (26). For C23H16ClN3O4 (433.84): C, 63.67; H, 3.72; Cl, 8.17; N, 9.69;found: C, 63.83; H, 3.54; N, 8.29.5-(4-Bromophenyl)-1,3-dimethylbenzo[G]pyrimido[4,5-b]quinoline-2,4,6,11(1h,3h,5h,12h)-tetraone (4j)
Orange powder; mp 229 °C. IR (KBr) (νmax/cm−1): 3398, 1705, 1656, 1575, 1511. 1H NMR (400 MHz, DMSO-d6): δH (ppm) 3.11 (s, 3H, NMe), 3.37 (s, 3H, NMe), 5.81 (s, 1H, CH), 7.18–7.91 (m, 8H, H-Ar), 13.12 (s, 1H, NH). 13C NMR (100 MHz, DMSO-d6): δC (ppm) 29.2, 32.3, 35.3, 89.0, 119.4, 124.1, 126.7, 127.0, 131.0, 131.2, 131.6, 132.4, 134.6, 135.6, 139.1, 151.0, 155.3, 156.4, 164.5, 181.8, 186.7. MS (EI, 70 eV): m/z (%): 477 (M+, 5), 338 (22), 321 (32), 235 (100), 156 (76), 76 (80). For C23H16BrN3O4 (478.29): C, 57.76; H, 3.37; N, 8.79; found: C, 57.87; H, 3.36; N, 8.84.1,3-Dimethyl-5-p-tolylbenzo[G]pyrimido[4,5-b]quinoline-2,4,6,11(1h,3h,5h,12h)-tetraone (4k)
Red powder; mp 263 °C. IR (KBr) (νmax/cm−1): 3359, 1720, 1657, 1568. 1H NMR (400 MHz, DMSO-d6): δH (ppm) 2.27 (s, 3H, Me), 3.11 (s, 3H, NMe), 3.33 (s, 3H, NMe), 5.52 (s, 1H, CH), 6.99 (d, JHH = 7.8 Hz, H-Ar), 7.21 (d, JHH = 7.9 Hz, H-Ar), 7.77–8.06 (m, 4H, H-Ar), 9.04 (s, 1H, NH). 13C NMR (100 MHz, DMSO-d6): δC (ppm) 22.8, 28.9, 31.7, 36.6, 88.7, 116.1, 124.4, 126.4, 126.8, 128.9, 130.8, 131.5, 134.5, 135.5135.7, 136.9, 139.4, 151.1, 158.1, 163.4, 181.7, 184.6. MS (EI, 70 eV): m/z (%): 413 (M+, 10), 322 (6), 275 (20), 235 (100), 156 (72), 76 (80). For C24H19N3O4 (413.43): C, 69.72; H, 4.63; N, 10.16; found: C, 69.79; H, 4.46; N, 10.20.1,3-Dimethyl-5-m-tolylbenzo[G]pyrimido[4,5-b]quinoline-2,4,6,11(1h,3h,5h,12h)-tetraone (4l)
Red powder; mp 195 °C. IR (KBr) (νmax/cm−1): 3327, 1705, 1656, 1569, 1529. 1H NMR (400 MHz, DMSO-d6): δH (ppm) 2.24 (s, 3H, Me), 3.17 (s, 3H, NMe), 3.38 (s, 3H, NMe), 5.82 (s, 1H, CH), 6.94–8.01 (m, 8H, H-Ar), 13.02 (s, 1H, NH). 13C NMR (100 MHz, DMSO-d6): δC (ppm) 22.5, 29.9, 31.2, 35.6, 86.8, 111.9, 124.7, 126.6, 127.0, 127.3, 128.2, 128.8, 131.5, 132.7, 134.3, 135.4, 135.3, 137.9, 139.2, 151.2, 155.3, 164.5, 181.8, 184.4. MS (EI, 70 eV): m/z (%): 413 (M+, 8), 275 (16), 257 (22), 235 (100). For C24H19N3O4 (413.43): C, 69.72; H, 4.63; N, 10.16; found: C, 69.85; H, 4.52; N, 10.07.The Royal Society of Chemistry apologises for these errors and any consequent inconvenience to authors and readers.
| This journal is © The Royal Society of Chemistry 2015 |