1094
H. Singh et al.
J 7.32, CH3), 1.05 (s, 3H, CH3), 0.91 (s, 3H, CH3); dC (100 MHz,
CDCl3) 195.68, 167.52, 159.83, 144.90, 156.37, 148.28, 143.90,
140.41, 130.35, 129.08, 122.24, 121.14, 114.72, 114.03, 112.10,
106.04, 61.86, 59.75, 55.59, 50.68, 40.86, 35.67, 32.63, 29.40,
27.15, 19.28, 14.21; nmax (KBr)/cmꢁ1 3341, 2959, 2930, 1682,
1633, 1608, 1518, 1505, 1486, 1379, 1218; Anal. Calc. for
C31H34N4O5: C 68.62, H 6.32, N 10.33 (m/z 542.2523). Found:
C 68.70, H 6.34, N 10.36 % (m/z (HRMS ESI) 543.2610
([M þ H]þ)).
Ethyl 2,7,7-Trimethyl-4-(4-((1-(naphthalen-1-yl)-1H-
1,2,3-triazol-4-yl)methoxy)phenyl)-5-oxo-1,4,5,6,7,8-
hexahydroquinoline-3-carboxylate (1g)
Pale-yellow solid, mp 988C, dH (400 MHz, CDCl3) 7.96–
7.92 (m, 3H, ArH), 7.58–7.49 (m, 5H, ArH), 7.23 (d, 2H, J 8.8,
ArH), 6.85 (d, 2H, J 8.8, ArH), 6.57 (s, 1H, NH), 5.28 and 5.24
(AB system, J 12.44, 2H, OCHa.Hb), 4.98 (s, 1H, CH), 4.04–
3.99 (q, 2H, J 7.32, OCH2), 2.32 (s, 3H, CH3), 2.27–2.04 (m,
4H), 1.17–1.14 (t, 3H, J 6.6, CH3), 1.00 (s, 3H, CH3), 0.86 (s, 3H,
CH3); dC (100 MHz, CDCl3) 195.70, 167.53, 156.40, 148.32,
144.39, 143.54, 140.48, 134.07, 133.50, 130.46, 129.09, 128.40,
128.24, 127.93, 127.08, 125.44, 124.93, 123.57, 122.21, 114.08,
112.06, 105.99, 61.90, 59.74, 50.65, 40.81, 35.67, 32.60, 29.39,
27.05, 19.24, 14.20 nmax (KBr)/cmꢁ1 3292, 2958, 2928, 1690,
1607, 1505, 1489, 1379, 1219; m/z (HRMS ESI) Calc. for
C34H34N4O4: 562.2574.Found: 563.2560 ([M þ H]þ).
Ethyl 2,7,7-Trimethyl-4-(4-((1-(4-nitrophenyl)-1H-
1,2,3-triazol-4-yl)methoxy)phenyl)-5-oxo-1,4,5,6,7,8-
hexahydroquinoline-3-carboxylate (1d)
Pale-yellow solid, mp 908C, dH (400 MHz, CDCl3) 8.38 (d,
2H, J 9.52, ArH), 8.15 (s, 1H, trizolyl-H), 7.96 (d, 2H, J 8.8,
ArH), 7.20 (d, 2H, J 8.8, ArH), 6.79 (d, 2H, J 8.8, ArH), 6.31 (s,
1H, NH), 5.20 and 5.16 (AB system, J 13.2, 2H, OCHa.Hb), 4.97
(s, 1H, CH), 4.05–4.0 (q, 2H, J 7.32, OCH2), 2.32 (s, 3H, CH3),
2.28–2.08 (m, 4H), 1.19–1.15 (t, 3H, J 6.6, CH3), 1.02 (s, 3H,
CH3), 0.89 (s, 3H, CH3); dC (100 MHz, CDCl3) 195.75, 167.50,
156.16, 148.34, 147.17, 146.18, 143.26, 141.10, 140.57, 129.15,
125.51, 120.79, 120.50, 113.99, 112.02, 106.13, 61.66, 59.80,
50.67, 40.88, 35.77, 32.65, 29.39, 27.13, 19.34, 14.21; nmax
(KBr)/cmꢁ1 3293, 2958, 2928, 1690, 1608, 1504, 1379, 1219;
m/z (HRMS ESI) Calc. for C30H31N5O6: 557.2268. Found:
558.2252 ([M þ H]þ).
Ethyl 2,7,7-Trimethyl-5-oxo-4-(4-((1-phenyl-1H-
1,2,3-triazol-4-yl)methoxy)phenyl)-1,4,5,6,7,8-
hexahydroquinoline-3-carboxylate (1h)
Pale-yellow solid, mp 1408C, dH (400 MHz, CDCl3) 8.01 (s,
1H, trizolyl-H), 7.71 (d, 2H, J 8.08, ArH), 7.51–7.43 (m, 3H,
ArH), 7.25–7.21 (m, 2H, ArH), 6.83 (d, 2H, J 8.8, ArH), 6.03 (s,
1H, NH), 5.21 (s, 2H, OCH2), 4.99 (s, 1H, CH), 4.07–4.02 (q,
2H, J 7.32, OCH2), 2.35 (s, 3H, CH3), 2.28–2.15 (m, 4H), 1.20–
1.16 (t, 3H, J 7.32, CH3), 1.05 (s, 3H, CH3), 0.91 (s, 3H, CH3); dC
(100 MHz, CDCl3) 195.78, 167.54, 156.32, 148.49, 145.12,
143.54, 140.46, 136.87, 129.73, 129.08, 128.84, 121.00,
120.57, 114.02, 112.02, 106.00, 61.82, 59.75, 50.64, 40.79,
35.68, 32.61, 29.65, 27.08, 19.23, 14.20; nmax (KBr)/cmꢁ1
3293, 2958, 2926, 1600, 1527, 1507, 1379, 1218; m/z (HRMS
ESI) Calc. for C30H32N4O4: 512.2418. Found: 513.2499
([M þ H]þ).
Ethyl 4-(4-((1-(4-Fluorophenyl)-1H-1,2,3-triazol-4-yl)
methoxy)phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-
hexahydroquinoline-3-carboxylate (1e)
Pale-yellow solid, mp 1028C, dH (400 MHz, CDCl3) 7.93 (s,
1H, trizolyl-H), 7.65–7.61 (m, 2H, ArH), 7.19–7.12 (m, 4H,
ArH), 6.76 (d, 2H, J 8.72, ArH), 6.36 (s, 1H, NH), 5.14 and 5.10
(AB system, J 12.36, 2H, OCHa.Hb), 4.92 (s, 1H, CH), 4.01–
3.95 (q, 2H, J 6.88, OCH2), 2.27 (s, 3H, CH3), 2.20–1.97 (m,
4H), 1.14–1.11 (t, 3H, J 7.32, CH3), 0.97 (s, 3H, CH3), 0.84 (s,
3H, CH3); dC (100 MHz, CDCl3) 195.86, 167.63, 156.43,
148.43, 145.42, 143.52, 140.58, 129.23, 122.74, 122.66,
121.27, 116.95, 116.72, 114.14, 112.19, 106.22, 61.91, 59.90,
50.80, 41.00, 35.84, 32.77, 29.52, 27.24, 19.43, 14.34; nmax
(KBr)/cmꢁ1 3292, 2959, 1686, 1608, 1517, 1507, 1489, 1380,
1220; Anal. Calc. for C30H31FN4O4: C 67.91, H 5.89, N 10.56
(m/z 530.2323). Found: C 68.02, H 5.88, N 10.59 % (m/z (HRMS
ESI) 531.2409 ([M þ H]þ)).
Ethyl 4-(4-((1-(3-Chlorophenyl)-1H-1,2,3-triazol-4-yl)
methoxy)phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-
hexahydroquinoline-3-carboxylate (1i)
Pale-yellow solid, mp 858C, dH (400 MHz, CDCl3) 8.04 (s,
1H, trizolyl-H), 7.77–7.76 (m, 1H, ArH), 7.62–7.60 (m, 1H,
ArH), 7.45–7.38 (m, 2H, ArH), 7.21 (d, 2H, J 8.24, ArH), 6.81
(d, 2H, J 8.72, ArH), 6.70 (s, 1H, NH), 5.18 and 5.15 (AB
system, J 12.44, 2H, OCHa.Hb), 4.98 (s, 1H, CH), 4.06–4.0 (q,
2H, J 6.88, OCH2), 2.31 (s, 3H, CH3), 2.06–2.24 (m, 4H), 1.19–
1.15 (t, 3H, J 7.32, CH3), 1.02 (s, 3H, CH3), 0.88 (s, 3H, CH3); dC
(100 MHz, CDCl3) 195.85, 167.46, 156.16, 147.71, 143.12,
140.41, 139.79, 135.58, 130.83, 129.44, 129.00, 128.88,
120.83, 118.53, 114.17, 114.08, 112.31, 106.25, 61.88, 59.79,
50.67, 41.10, 35.72. 32.71, 29.38, 27.18, 19.43, 14.21; nmax
(KBr)/cmꢁ1 3291, 2929, 1686, 1608, 1507, 1490, 1379, 1218;
m/z (HRMS ESI) Calc. for C30H31ClN4O4: 546.2034. Found:
547.2028 ([M þ H])þ.
Ethyl 4-(4-((1-(3-Chloro-4-fluorophenyl)-1H-1,2,3-
triazol-4-yl)methoxy)phenyl)-2,7,7-trimethyl-5-oxo-
1,4,5,6,7,8-hexahydroquinoline-3-carboxylate (1f)
Pale-yellow solid, mp 1308C, dH (400 MHz, CDCl3) 8.05 (s,
1H, trizolyl-H), 7.86–7.83 (m, 1H, ArH), 7.63–7.59 (m, 1H,
ArH), 7.31–7.20 (m, 3H, ArH), 6.81 (d, 2H, J 9.16, ArH), 6.35
(s, 1H, NH), 5.20 and 5.17 (AB system, J 13.2, 2H, OCHa.Hb),
4.99 (s, 1H, CH), 4.07–4.02 (q, 2H, J 6.6, OCH2), 2.41 (s, 3H,
CH3), 2.24–2.05 (m, 4H), 1.21–1.17 (t, 3H, J 7.36, CH3), 1.04 (s,
3H, CH3), 0.91 (s, 3H, CH3); dC (100 MHz, CDCl3) 195.74,
167.50, 156.24, 148.37, 145.63, 143.30, 140.48, 129.12, 128.97,
123.07, 120.98, 120.33, 120.25, 117.74, 117.52, 114.01, 112.08,
106.14, 61.73, 59.79, 50.66, 40.92, 35.73, 32.66, 29.39, 27.13,
19.33, 14.21; nmax (KBr)/cmꢁ1 3293, 2960, 1686, 1608, 1507,
1380, 1219; Anal. Calc. for C30H30ClFN4O4: C 63.77, H 5.35,
N 9.92 (m/z 564.1934). Found: C 63.90, H 5.33, N 9.91 % (m/z
(HRMS ESI) 565.2015 ([M þ H]þ)).
Ethyl 2-Methyl-4-(4-((1-(4-nitrophenyl)-1H-1,2,3-triazol-
4-yl)methoxy)phenyl)-5-oxo-1,4,5,6,7,8-
hexahydroquinoline-3-carboxylate (1j)
Yellow solid, mp 2278C, dH (400 MHz, CDCl3) 8.40 (d, 2H,
J 8.8, ArH), 8.12 (s, 1H, trizolyl-H), 7.97 (d, 2H, J 8.8, ArH),
7.25–7.21 (m, 2H, ArH), 6.82 (d, 2H, J 8.8, ArH), 5.80 (s, 1H,
NH), 5.26 and 5.22 (AB system, J 13.16, 2H, OCHa.Hb), 5.02 (s,
1H, CH), 4.07–4.01 (q, 2H, J 7.32, OCH2), 2.45–2.28 (m, 7H),
2.05–1.89 (m, 2H, CH2), 1.19–1.16 (t, 3H, J 7.32, CH3); dC
(100 MHz, CDCl3) 195.81, 167.32, 156.19, 149.18, 146.89,