M. Bakthadoss, A. Devaraj, D. Kannan
FULL PAPER
43.59, 51.50, 52.45, 79.94, 97.26, 119.57, 112.58, 123.51, 124.10, Methyl 11-(2H-1,3-Benzodioxol-5-yl)-16-methyl-8-[(4-methylphen-
125.26, 125.44, 125.54, 125.87, 126.40, 126.66, 126.82, 129.03, yl)sulfonyl]-14-phenyl-12-oxa-8,14,15-triazatetracyclo[8.7.0.02,7
129.10, 130.06, 130.35, 130.44, 131.02, 133.65, 134.16, 135.72, 013,17]heptadeca-2(7),3,5,13(17),15-pentaene-10-carboxylate (10g):
.
138.40, 144.17, 145.95, 148.08, 170.64 ppm. MS: m/z = 657 [M+
1]. C39H33N3O5S (655.77): calcd. C 71.43, H 5.07, N 6.41; found
C 71.53, H 5.01, N 6.52.
+
Yield 0.605 g (93%); colorless solid; m.p. 240–242 °C. IR (neat): ν
˜
= 1785, 1576, 1530 cm–1. 1H NMR (300 MHz, CDCl3): δ = 1.49
(s, 3 H), 2.18 (s, 3 H), 3.40 (s, 3 H), 3.86 (d, J = 12.3 Hz, 1 H),
4.19 (d, J = 12.3 Hz, 1 H), 4.50 (s, 1 H), 5.44 (s, 1 H), 6.03 (d, J =
4.5 Hz, 2 H), 6.80–7.95 (m, 16 H) ppm. 13C NMR (75 MHz,
CDCl3): δ = 13.79, 21.35, 40.53, 42.79, 52.33, 52.75, 84.20, 96.89,
101.48, 106.90, 108.41, 119.64, 120.51, 123.69, 124.09, 125.60,
126.33, 128.15, 128.80, 129.13, 129.42, 130.72, 134.11, 135.89,
138.33, 144.14, 145.80, 147.57, 148.06, 148.38, 171.48 ppm. MS:
m/z = 651 [M+ + 1]. C36H31N3O7S (649.72): calcd. C 66.55, H 4.81,
N 6.47; found C 66.63, H 4.70, N 6.58.
Methyl 16-Methyl-8-[(4-methylphenyl)sulfonyl]-11-(2-methylphenyl)-
14-phenyl-12-oxa-8,14,15-triazatetracyclo[8.7.0.02,7.013,17]hepta-
deca-2(7),3,5,13(17),15-pentaene-10-carboxylate (10c): Yield
0.576 g (93 %); colorless solid; m.p. 230–232 °C. IR (neat): ν =
˜
1
1735, 1596, 1510 cm–1. H NMR (300 MHz, CDCl3): δ = 1.57 (s,
3 H), 2.21 (s, 3 H), 2.29 (s, 3 H), 3.28 (s, 3 H), 4.10–4.14 (m, 1 H),
4.53–4.62 (m, 2 H), 5.78 (s, 1 H), 6.93–7.95 (m, 17 H) ppm. 13C
NMR (75 MHz, CDCl3): δ = 13.90, 19.41, 21.40, 40.85, 43.40,
51.39, 52.63, 81.13, 97.27, 119.63, 123.56, 124.10, 125.53, 126.31,
126.63, 127.32, 128.70, 129.07, 129.33, 129.43, 130.93, 131.14,
132.85, 134.06, 135.67, 136.11, 138.34, 144.18, 145.87, 171.16 ppm.
MS: m/z = 620 [M+ + 1]. C36H33N3O5S (619.73): calcd. C 69.77,
H 5.37, N 6.78; found C 69.85, H 5.30, N 6.84.
Methyl 11-(4-Fluorophenyl)-16-methyl-8-[(4-methylphenyl)sulfonyl]-
14-phenyl-12-oxa-8,14,15-triazatetracyclo[8.7.0.02,7.013,17]hepta-
deca-2(7),3,5,13(17),15-pentaene-10-carboxylate (10h): Yield
0.569 g (91 %); colorless solid; m.p. 224–226 °C. IR (neat): ν =
˜
1
1792, 1586, 1546 cm–1. H NMR (300 MHz, CDCl3): δ = 1.49 (s,
3 H), 2.20 (s, 3 H), 3.38 (s, 3 H), 3.90 (d, J = 12.3 Hz, 1 H), 4.13
(d, J = 12.3 Hz, 1 H), 4.52 (s, 1 H), 5.53 (s, 1 H), 6.91–7.95 (m, 17
H) ppm. 13C NMR (75 MHz, CDCl3): δ = 13.94, 21.53, 40.48,
42.65, 52.25, 52.82, 83.75, 96.80, 115.77, 116.05, 119.68, 123.63,
124.16, 125.70, 126.31, 128.41, 128.52, 128.86, 129.15, 129.44,
130.43, 130.75, 134.10, 135.85, 138.28, 144.19, 145.85, 147.50,
171.54 ppm. MS: m/z = 625 [M+ + 1]. C35H30FN3O5S (623.70):
calcd. C 67.40, H 4.85, N 6.74; found C 67.51, H 4.93, N 6.66.
Methyl 16-Methyl-8-[(4-methylphenyl)sulfonyl]-14-phenyl-11-[4-
(propan-2-yl)phenyl]-12-oxa-8,14,15-triazatetracyclo[8.7.0.02,7
.
013,17]heptadeca-2(7),3,5,13(17),15-pentaene-10-carboxylate (10d):
Yield 0.609 g (94%); colorless solid; m.p. 227–229 °C. IR (neat): ν
˜
= 1738, 1592, 1518 cm–1. 1H NMR (300 MHz, CDCl3): δ = 1.27
(d, J = 6.9 Hz, 6 H), 1.50 (s, 3 H), 2.19 (s, 3 H), 2.94 (sept, J =
6.9 Hz, 1 H), 3.37 (s, 3 H), 3.89 (d, J = 12.6 Hz, 1 H), 4.15 (d, J =
12.3 Hz, 1 H), 4.53 (s, 1 H), 5.52 (s, 1 H), 6.90–7.95 (m, 17 H) ppm.
13C NMR (75 MHz, CDCl3): δ = 13.84, 21.39, 23.82, 23.96, 33.89,
40.43, 42.73, 52.24, 52.57, 84.21, 96.81, 119.64, 123.68, 124.07,
125.53, 126.33, 126.47, 126.84, 128.76, 129.16, 129.41, 130.76,
131.82, 134.10, 135.93, 138.38, 144.13, 145.80, 147.77, 150.17,
171.48 ppm. MS: m/z = 649 [M+ + 1]. C38H37N3O5S (647.79):
calcd. C 70.46, H 5.76, N 6.49; found C 70.54, H 5.63, N 6.60.
Methyl 11-(2-Chlorophenyl)-16-methyl-8-[(4-methylphenyl)sulfonyl]-
14-phenyl-12-oxa-8,14,15-triazatetracyclo[8.7.0.02,7.013,17]hepta-
deca-2(7),3,5,13(17),15-pentaene-10-carboxylate (10i): Yield 0.602 g
(94%); colorless solid; m.p. 230–232 °C. IR (neat): ν = 1789, 1566,
˜
1556 cm–1. 1H NMR (300 MHz, CDCl3): δ = 1.49 (s, 3 H), 2.20 (s,
3 H), 3.41 (s, 3 H), 3.88 (d, J = 12.3 Hz, 1 H), 4.07 (d, J = 12.6 Hz,
1 H), 4.53 (s, 1 H), 5.54 (s, 1 H), 6.91–7.90 (m, 17 H) ppm. 13C
NMR (75 MHz, CDCl3): δ = 13.68, 21.39, 40.24, 42.42, 52.06,
52.60, 83.42, 96.77, 119.49, 123.39, 124.18, 125.60, 126.12, 126.16,
127.83, 128.48, 128.77, 128.98, 129.06, 129.38, 130.64, 132.98,
133.98, 135.24, 135.66, 138.15, 144.16, 145.67, 147.28, 171.93 ppm.
MS: m/z = 641 [M+ + 1]. C35H30ClN3O5S (640.15): calcd. C 65.67,
H 4.72, N 6.56; found C 65.78, H 4.63, N 6.63.
Methyl 11-(2-Methoxyphenyl)-16-methyl-8-[(4-methylphenyl)sulf-
onyl]-14-phenyl-12-oxa-8,14,15-triazatetracyclo[8.7.0.02,7.013,17]hep-
tadeca-2(7),3,5,13(17),15-pentaene-10-carboxylate (10e): Yield
0.585 g (92 %); colorless solid; m.p. 238–240 °C. IR (neat): ν =
˜
1
1745, 1586, 1520 cm–1. H NMR (300 MHz, CDCl3): δ = 1.54 (s,
3 H), 2.22 (s, 3 H), 3.37 (s, 3 H), 3.79 (s, 3 H), 4.04 (d, J = 12.3 Hz,
1 H), 4.36 (d, J = 12.3 Hz, 1 H), 4.71 (s, 1 H), 5.95 (s, 1 H), 6.89–
7.93 (m, 17 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 14.01, 21.53,
39.25, 43.76, 51.35, 52.38, 55.30, 78.33, 96.95, 110.32, 119.58,
121.05, 123.18, 123.52, 123.99, 125.42, 126.38, 127.29, 127.94,
128.44, 129.05, 129.38, 130.38, 131.10, 134.12, 135.68, 138.45,
Methyl 11-(3-Chlorophenyl)-16-methyl-8-[(4-methylphenyl)sulfonyl]-
14-phenyl-12-oxa-8,14,15-triazatetracyclo[8.7.0.02,7.013,17]hepta-
deca-2(7),3,5,13(17),15-pentaene-10-carboxylate (10j): Yield 0.576 g
(90%); colorless solid; m.p. 230–232 °C. IR (neat): ν = 1758, 1591,
˜
1
1538 cm–1. H NMR (300 MHz, CDCl3): δ = 1.49 (3 H), 2.21 (s, 3
144.09, 145.89, 147.95, 156.37, 170.40 ppm. MS: m/z = 637 [M+
+
H), 3.39 (s, 3 H), 3.89 (d, J = 12.3 Hz, 1 H), 4.11 (d, J = 12.3 Hz,
1 H), 4.52 (s, 1 H), 5.53 (s, 1 H), 6.91–7.94 (m, 17 H) ppm. 13C
NMR (75 MHz, CDCl3): δ = 13.84, 21.60, 40.63, 42.68, 52.13,
52.92, 83.62, 96.81, 119.67, 123.63, 124.17, 125.73, 126.19, 126.31,
127.96, 128.89, 129.10, 129.16, 129.45, 130.74, 133.04, 134.12,
135.45, 135.45, 135.84, 138.26, 144.19, 145.85, 147.41, 171.49 ppm.
MS: m/z = 641 [M+ + 1]. C35H30ClN3O5S (640.15): calcd. C 65.67,
H 4.72, N 6.56; found C 65.56, H 4.63, N 6.62.
1]. C36H33N3O6S (635.73): calcd. C 68.01, H 5.23, N 6.61; found
C 68.11, H 5.16, N 6.70.
Methyl 11-(4-Methoxyphenyl)-16-methyl-8-[(4-methylphenyl)sulf-
onyl]-14-phenyl-12-oxa-8,14,15-triazatetracyclo[8.7.0.02,7.013,17]hep-
tadeca-2(7),3,5,13(17),15-pentaene-10-carboxylate (10f): Yield
0.604 g (95 %); colorless solid; m.p. 237–239 °C. IR (neat): ν =
˜
1
1736, 1591, 1528 cm–1. H NMR (300 MHz, CDCl3): δ = 1.49 (s,
3 H), 2.19 (s, 3 H), 3.37 (s, 3 H), 3.84 (s, 3 H), 3.91 (d, J = 12.6 Hz,
1 H), 4.17 (d, J = 12.3 Hz, 1 H), 4.51 (s, 1 H), 5.49 (s, 1 H), 6.90–
Methyl 11-(4-Chlorophenyl)-16-methyl-8-[(4-methylphenyl)sulfonyl]-
14-phenyl-12-oxa-8,14,15-triazatetracyclo[8.7.0.02,7.013,17]hepta-
7.95 (m, 17 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 13.84, 21.40, deca-2(7),3,5,13(17),15-pentaene-10-carboxylate (10k): Yield
40.44, 42.76, 52.34, 52.60, 55.33, 84.13, 96.83, 114.16, 119.63, 0.595 g (93 %); colorless solid; m.p. 228–230 °C. IR (neat): ν =
˜
1
123.61, 124.65, 125.53, 126.32, 126.47, 126.54, 127.90, 128.75, 1745, 1588, 1529 cm–1. H NMR (300 MHz, CDCl3): δ = 1.52 (s,
129.08, 129.41, 130.74, 134.21, 135.95, 138.41, 144.10, 145.81, 3 H), 2.21 (s, 3 H), 3.40 (s, 3 H), 4.11 (d, J = 12 Hz, 1 H), 4.44 (d,
147. 84, 160. 29, 171.63 ppm. MS: m/z = 637 [M+ + 1].
C36H33N3O6S (635.73): calcd. C 68.01, H 5.23, N 6.61; found C
68.09, H 5.14, N 6.72.
J = 12 Hz, 1 H), 4.71 (s, 1 H), 6.02 (s, 1 H), 6.91–7.92 (m, 17
H) ppm. 13C NMR (75 MHz, CDCl3): δ = 13.90, 21.42, 39.64,
43.69, 51.16, 52.90, 80.26, 97.17, 119.72, 123.43, 124.14, 125.65,
1510
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Eur. J. Org. Chem. 2014, 1505–1513