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Na2SO4, ltered, and concentrated under reduced pressure. The
crude product was puried by manual column chromatography
using CH2Cl2/MeOH gradient to obtain the quinoline-3-
carboxamides 11a–g in yields ranging from 51% to 89% and
further puried by recrystallisation from DCM.
N-(1-Adamantanyl)-6-chloro-4-oxo-1,4-dihydroquinoline-3-
carboxamide (11a). White solid, yield: 84%. 1H NMR (DMSO-d6)
d 1.67 (s, 6H), 2.06 (s, 9H), 7.72 (d, J ¼ 8.8 Hz, 1H), 7.79 (dd, J ¼
8.8, 2.4 Hz, 1H), 8.17 (d, J ¼ 2.4 Hz, 1H), 8.71 (s, 1H), 9.85 (s, 1H),
12.76 (s, 1H); 13C NMR (DMSO-d6) d 29.3, 36.5, 41.9, 51.0, 112.5,
121.9, 124.8, 127.7, 129.9, 133.1, 138.2, 144.1, 163.2, 175.4;
HRMS (ESI) m/z calcd for C20H21ClN2O2 ([M + H]+) m/z 357.1364;
found 357.1362.
N-(1-Adamantanyl)-8-chloro-4-oxo-1,4-dihydroquinoline-3-
carboxamide (11b). White solid, yield: 56%. 1H NMR (DMSO-d6)
d 1.67 (s, 6H), 2.06 (s, 9H), 7.47 (t, J ¼ 7.9 Hz, 1H), 7.95 (dd, J ¼
7.7, 1.3 Hz, 1H), 8.22 (dd, J ¼ 8.2, 1.3 Hz, 1H), 8.64 (s, 1H), 9.80
(s, 1H), 12.24 (s, 1H); 13C NMR (DMSO-d6) d 29.4, 36.5, 41.9,
51.1, 112.9, 122.7, 125.3, 125.4, 128.2, 132.9, 136.1, 144.4, 162.9,
176.3; HRMS (ESI) m/z calcd for C20H21ClN2O2 ([M + H]+) m/z
357.1364; found 357.1359.
4.1.8. General procedure for the synthesis of 13a–g and
15a–d. Title compounds were prepared following the general
amide coupling protocol used for obtaining compounds 8a–k.
The crude product was puried by ash column chromatog-
raphy using CH2Cl2/MeOH gradient to obtain the title
compounds in yields ranging from 31% to 92%. Compounds
13a–d were further puried by recrystallisation from acetone.
Compounds 13e,f and 15a,c,d were already >95% pure aer
ash chromatography, while compounds 13g and 15b were
further puried by preparative HPLC. 1H NMR data of
compounds 13a–c matched those which were reported in the
literature.47,58
N-Cyclooctylquinoline-2-carboxamide (13a).47 White solid,
yield: 46%. 1H NMR (DMSO-d6) d 1.41–1.98 (m, 14H), 3.96–4.21
(m, 1H), 7.72 (dd, J ¼ 8.1, 7.0 Hz, 1H), 7.87 (dd, J ¼ 8.3, 7.0 Hz,
1H), 8.08 (d, J ¼ 8.1 Hz, 1H), 8.16 (dd, J ¼ 8.4, 6.1 Hz, 2H), 8.56
(d, J ¼ 8.5 Hz, 1H), 8.60 (d, J ¼ 8.3 Hz, 1H).
N-(1-Adamantanyl)-2-quinoline-2-carboxamide (13b).58 White
solid, yield: 65%. 1H NMR (DMSO-d6) d 1.69 (s, 6H), 2.10 (s, 3H),
2.13 (s, 6H), 7.71 (ddd, J ¼ 8.1, 6.9, 1.2 Hz, 1H), 7.86 (ddd, J ¼
8.4, 6.9, 1.4 Hz, 1H), 8.05–8.16 (m, 4H), 8.56 (d, J ¼ 8.4 Hz, 1H).
N-Cyclooctyl-2-naphthamide (13c).47 White solid, yield: 56%.
1H NMR (DMSO-d6) d 1.42–1.89 (m, 14H), 3.94–4.21 (m, 1H),
7.54–7.63 (m, 2H), 7.89–8.04 (m, 4H), 8.38 (d, J ¼ 7.8 Hz, 1H),
8.42 (s, 1H).
N-(1-Adamantanyl)-7,8-dichloro-4-oxo-1,4-dihydroquinoline-3-
carboxamide (11c). White solid, yield: 68%. 1H NMR (DMSO-d6)
d 1.69 (s, 6H), 2.08 (s, 9H), 7.62 (d, J ¼ 8.7 Hz, 1H), 8.21 (d, J ¼
9.0 Hz, 1H), 8.66 (s, 1H), 9.72 (s, 1H), 12.29 (s, 1H); 13C NMR
(DMSO-d6) d 29.4, 36.5, 41.9, 51.1, 113.2, 121.4, 125.9, 126.0,
126.5, 136.3, 137.8, 145.1, 162.8, 175.9; HRMS (ESI) m/z calcd for
N-(1-Adamantanyl)-2-naphthamide (13d). White solid, yield:
60%. 1H NMR (DMSO-d6) d 1.68 (s, 6H), 2.07 (s, 3H), 2.12 (s, 6H),
7.62–7.53 (m, 2H), 7.76 (s, 1H), 7.85 (dd, J ¼ 8.6, 1.6 Hz, 1H),
7.93–8.01 (m, 3H), 8.36 (s, 1H); 13C NMR (DMSO-d6) d 29.4, 36.6,
41.4, 52.1, 125.1, 127.0, 127.71, 127.74, 128.0 (2C), 129.2, 132.6,
133.8, 134.4, 166.6; HRMS (ESI) m/z calcd for C21H23NO ([M +
H]+) m/z 306.1852; found 306.1844.
C
20H20Cl2N2O2 ([M + H]+) m/z 391.0975; found 391.0971.
N-(1-Adamantanyl)-6,8-dichloro-4-oxo-1,4-dihydroquinoline-3-
carboxamide (11d). White solid, yield: 89%. 1H NMR (DMSO-d6)
d 1.67 (s, 6H), 2.06 (s, 9H), 8.05–8.22 (m, 2H), 8.63 (s, 1H), 9.70
(s, 1H), 12.41 (s, 1H); 13C NMR (DMSO-d6) d 29.4, 36.5, 41.8,
51.2, 113.2, 124.2, 124.5, 128.7, 129.6, 132.4, 135.1, 144.6, 162.6,
175.2; HRMS (ESI) m/z calcd for C20H20Cl2N2O2 ([M + H]+) m/z
391.0975; found 391.0973.
N-(1-Adamantanyl)-5-bromo-2-naphthamide (13e). White solid,
yield: 52%. 1H NMR (DMSO-d6) d 1.69 (s, 6H), 2.09 (s, 3H), 2.14
(s, 6H), 7.50 (dd, J ¼ 8.5, 7.5 Hz, 1H), 7.58 (dd, J ¼ 7.0, 1.0 Hz,
1H), 7.69 (dd, J ¼ 8.5, 7.1 Hz, 1H), 7.93 (dd, J ¼ 7.4, 0.9 Hz, 1H),
8.05–8.14 (m, 2H), 8.21 (d, J ¼ 8.5 Hz, 1H); 13C NMR (DMSO-d6)
d 29.4, 36.6, 41.4, 52.3, 122.5, 126.0, 126.1, 127.5, 127.7 (2C),
130.8, 131.5, 131.6, 137.6, 168.2; HRMS (ESI) m/z calcd for
N-(1-Adamantanyl)-5,8-chloro-4-oxo-1,4-dihydroquinoline-3-
carboxamide (11e). White solid, yield: 51%. 1H NMR (DMSO-d6)
d 1.67 (s, 6H), 2.05 (s, 9H), 7.43 (d, J ¼ 8.4 Hz, 1H), 7.86 (d, J ¼
8.4 Hz, 1H), 8.58 (s, 1H), 9.67 (s, 1H), 12.07 (s, 1H); 13C NMR
(DMSO-d6) d 29.3, 36.5, 41.8, 51.1, 114.2, 121.9, 123.9, 128.0,
132.5, 132.7, 138.5, 144.1, 162.6, 176.3; HRMS (ESI) m/z calcd for
C
21H22BrNO ([M + H]+) m/z 384.0958; found 384.0956.
N-(1-Adamantanyl)-6-bromo-2-naphthamide (13f). White solid,
20H20Cl2N2O2 ([M + H]+) m/z 391.0975; found 391.0976.
yield: 31%. 1H NMR (DMSO-d6) d 1.68 (s, 6H), 2.07 (s, 3H), 2.11
(s, 6H), 7.69 (dd, J ¼ 8.7, 1.9 Hz, 1H), 7.80 (s, 1H), 7.88–7.99 (m,
3H), 8.25 (s, 1H), 8.37 (s, 1H); 13C NMR (DMSO-d6) d 29.4, 36.6,
41.4, 52.1, 121.1, 126.2, 127.3, 127.7, 130.0, 130.1, 131.1, 131.4,
134.4, 135.5, 166.4; HRMS (ESI) m/z calcd for C21H22BrNO ([M +
H]+) m/z 384.0958; found 384.0960.
C
N-(1-Adamantanyl)-5,7-dichloro-4-oxo-1,4-dihydroquinoline-3-
carboxamide (11f). White solid, yield: 64%. 1H NMR (DMSO-d6)
d 1.67 (s, 6H), 2.05 (s, 9H), 7.53 (d, J ¼ 2.0 Hz, 1H), 7.65 (d, J ¼
2.1 Hz, 1H), 8.66 (s, 1H), 9.74 (s, 1H), 12.66 (s, 1H); 13C NMR
(DMSO-d6) d 29.3, 36.5, 41.8, 51.0, 114.1, 118.1, 121.5, 127.4,
134.9, 136.5, 142.6, 143.9, 162.9, 176.0; HRMS (ESI) m/z calcd for
N-(1-Adamantanyl)-6-methoxy-2-naphthamide (13g). White
solid, yield: 52%. 1H NMR (DMSO-d6) d 1.67 (s, 6H), 2.07 (s, 3H),
2.11 (s, 6H), 3.89 (s, 3H), 7.21 (dd, J ¼ 9.0, 2.5 Hz, 1H), 7.35 (d, J
¼ 2.4 Hz, 1H), 7.66 (s, 1H), 7.83 (s, 2H), 7.90 (d, J ¼ 9.0 Hz, 1H),
8.30 (s, 1H); 13C NMR (DMSO-d6) d 29.4, 36.6, 41.4, 52.0, 55.7,
106.3, 119.6, 125.5, 126.8, 127.6, 127.9, 130.8, 131.5, 136.0,
158.8, 166.6; HRMS (ESI) m/z calcd for C22H25NO ([M + H]+) m/z
336.1958; found 336.1951.
C
20H20Cl2N2O2 ([M + H]+) m/z 391.0975; found 391.0974.
N-(1-Adamantanyl)-7-bromo-4-oxo-1,4-dihydroquinoline-3-
carboxamide (11g). White solid, yield: 75%. 1H NMR (DMSO-d6)
d 1.67 (s, 6H), 2.06 (s, 9H), 7.61 (dd, J ¼ 8.7, 1.6 Hz, 1H), 7.88 (d, J
¼ 1.8 Hz, 1H), 8.14 (d, J ¼ 8.7 Hz, 1H), 8.70 (s, 1H), 9.86 (s, 1H),
12.59 (s, 1H); 13C NMR (DMSO-d6) d 29.3, 36.5, 41.9, 51.0, 112.7,
121.6, 125.5, 126.4, 128.2, 128.3, 140.5, 144.3, 163.2, 176.2;
HRMS (ESI) m/z calcd for C20H21BrN2O2 ([M + H]+) m/z 401.0859;
found 401.0859.
7536 | RSC Adv., 2020, 10, 7523–7540
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