3-(4-Methoxyphenyl)-9-(1,1-dioxytetrahydrothien-3-yl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one
(4). C H NO S. Yield 69%, mp 203–204°C (propan-2-ol:hexane). PMR spectrum (300 MHz, CDCl , δ, ppm, J/Hz): 3.85
22 21
6
3
3
3
3
(3H, s, OMe-4′), 4.19, 4.34 (each 1H, d, J = 18, CH -10), 5.0, 5.06 (each 1H, d, J = 9.0, CH -8), 6.87 (1H, d, J = 8.7, H-6),
6.98 (2H, d, J = 9, H-3′, H-5′), 7.49 (2H, d, J = 9, H-2′, H-6′), 7.92 (1H, s, H-2), 8.10 (1H, d, J = 8.7, H-5); sulfolane protons:
2
2
3
3
3
2.26, 2.53 (each 1H, m, CH -4), 3.08, 3.45 (each 2H, m, CH -2, CH -5), 3.80 (1H, m, CH-3).
2
2
2
3-(3,4-Dimethoxyphenyl)-9-(2-methoxyethyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one (5).
C H NO . Yield 73%, mp 103–104°C (toluene:hexane). PMR spectrum (300 MHz, CDCl , δ, ppm, J/Hz): 3.91, 3.93 (each
22 23
6
3
3
3
3H, s, OMe-3′, OMe-4′), 4.26 (2H, s ,CH -10), 5.01 (2H, s, CH -8), 6.88 (1H, d, J = 8.7, H-6), 6.93 (1H, d, J = 8.3, H-5′),
7.05 (1H, dd, J = 8.3, J = 2.0, H-6′), 7.21 (1H, d, J = 2.0, H-2′), 7.95 (1H, s, H-2), 8.08 (1H, d, J = 8.7, H-5); amine protons:
2
2
3
4
4
3
2.99, 3.60 [each 2H, m, N(9)-(CH ) ], 3.41 (3H, s, OMe).
2 2
9-(3-Methoxypropyl)-3-(3,4-dimethoxyphenyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one (6).
C H NO . Yield 81%, mp 107–108°C (toluene:hexane). PMR spectrum (300 MHz, CDCl , δ, ppm, J/Hz): 3.91, 3.93 (each
23 25
6
3
3
3
3H, s, OMe-3′, OMe-4′), 4.18 (2H, s, CH -10), 4.97 (2H, s, CH -8), 6.87 (1H, d, J = 8.7, H-6), 6.93 (1H, d, J = 8.3, H-5′),
7.05 (1H, dd, J = 8.3, J = 2.0, H-6′), 7.21 (1H, d, J = 2.0, H-2′), 7.94 (1H, s, H-2), 8.08 (1H, d, J = 8.7, H-5); amine protons:
2
2
3
4
4
3
2.86, 1.86, 3.47 [each 2H, m, N(9)-(CH ) ], 3.34 (3H, s, OMe).
2 3
3-(4-Methoxyphenyl)-9-[2-(2-methoxyphenyl)ethyl]-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one (7).
C H NO . Yield 84%, mp 120–121°C (propan-2-ol:hexane). PMR spectrum (300 MHz, CDCl , δ, ppm, J/Hz): 3.84 (3H,
27 25
5
3
3
3
s, OMe-4′), 4.24 (2H, s, CH -10), 4.99 (2H, s, CH -8), 6.97 (2H, d, J = 9, H-3′, H-5′), 7.50 (2H, d, J = 9, H-2′, H-6′), 7.92
(1H, s, H-2), 8.07 (1H, d, J = 8.7, H-5); amine protons: 2.87-3.06 [4H, m, N(9)-(CH ) ], 3.78 (3H, s, OMe-2), 6.87, 7.17 (5H,
2
2
3
2 2
2m, H-6, Ar′).
3-(3,4-Dimethoxyphenyl)-9-(3-phenylpropyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one (8).
C H NO . Yield 75%, mp 99–100°C (propan-2-ol:hexane). PMR spectrum (300 MHz, CDCl , δ, ppm, J/Hz): 1.92, 2.70,
28 27
5
3
2.78 [each 2H, m, N-(CH ) ], 3.91, 3.93 (each 3H, s, OMe-3′, OMe-4′), 4.18 (2H, s, CH -10), 4.98 (2H, s, CH -8), 6.87
2 2
2
2
3
3
3
4
(1H, d, J = 8.7, H-6), 6.93 (1H, d, J = 8.3, H-5′), 7.04 (1H, dd, J = 8.3, J = 2.4, H-6′), 7.21, 7.29 (6H, 2m, Ph, H-2′), 7.95
(1H, s, H-2), 8.08 (1H, d, J = 8.7, H-5).
3
3-(4-Methoxyphenyl)-9-(2-morpholin-4-ylethyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one (9).
C H N O . Yield 79%, mp 176–177°C (propan-2-ol:hexane). PMR spectrum (300 MHz, CDCl , δ, ppm, J/Hz): 3.84 (3H,
24 26
2
5
3
3
3
s, OMe-4′), 4.24 (2H, s, CH -10), 5.0 (2H, s, CH -8), 6.86 (1H, d, J = 8.7, H-6), 6.97 (2H, d, J = 9, H-3′, H-5′), 7.49 (2H, d,
J = 9, H-2′, H-6′), 7.92 (1H, s, H-2), 8.08 (1H, d, J = 8.7, H-5); amine protons: 2.61, 2.93 [each 2H, m, N(9)-(CH ) ], 2.48
2
2
3
3
2 2
[4H, m, N(CH ) ], 3.71 [4H, m, O(CH ) ].
2 2
2 2
3-(3,4-Dimethoxyphenyl)-9-(3-morpholin-4-ylpropyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one
(10). C H N O . Yield 72%, mp 112–113°C (propan-2-ol:hexane). PMR spectrum (300 MHz, CDCl , δ, ppm, J/Hz): 3.91,
26 30
2
6
3
3
3.93 (each 3H, s, OMe-3′, OMe-4′), 4.19 (2H, s, CH -10), 4.97 (2H, s, CH -8), 6.87 (1H, d, J = 8.7, H-6), 6.93 (1H, d,
J = 8.3, H-5′), 7.04 (1H, dd, J = 8.3, J = 2.0, H-6′), 7.21 (1H, d, J = 2.0, H-2′), 7.95 (1H, s, H-2), 8.08 (1H, d, J = 8.7,
H-5); amine protons: 1.78, 2.81 [each 2H, m, N(9)-(CH ) ], 2.45 [6H, m, 4H of morpholine N(CH ) and 2H of N(9)-(CH ) ],
2
2
3
3
4
4
3
2 3
2 2
2 3
3.72 [4H, m, O(CH ) ].
2 2
3-(4-Methoxyphenyl)-9-(pyridin-4-ylmethyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one (11).
C H N O . Yield 78%, mp 163–164°C (propan-2-ol). PMR spectrum (300 MHz, CDCl , δ, ppm, J/Hz): 3.83 (3H, s,
24 20
2
4
3
3
OMe-4′), 4.16 (2H, s, CH -10), 5.0 (2H, s, CH -8), 6.92 (1H, d, J = 8.7, H-6), 6.96 (2H, m, H-3′, H-5′), 7.47 (2H, m, H-2′,
H-6′), 7.86 (1H, s, H-2), 8.11 (1H, d, J = 8.7, H-5); amine protons: 3.97 [2H, s, N(9)CH ], 7.34 (2H, m, H-3′′, H-5′′), 8.61
2
2
3
2
(2H, m, H-2′′, H-6′′).
3-(4-Methoxyphenyl)-9-(2-furylmethyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one (12).
C H NO . Yield 73%, mp 146–147°C (propan-2-ol:hexane). PMR spectrum (300 MHz, CDCl , δ, ppm, J/Hz): 3.84 (3H,
23 19
5
3
3
s, OMe-4′), 3.94 [2H, s, N(9)-CH ], 4.22 (2H, s, CH -10), 4.99 (2H, s, CH -8), 6.91 (1H, d, J = 8.7, H-6), 6.97 (2H, d,
2
2
2
3
3
3
J = 9, H-3′, H-5′), 7.49 (2H, d, J = 9, H-2′, H-6′), 7.91 (1H, s, H-2), 8.10 (1H, d, J = 8.7, H-5); furan protons: 6.30, 6.36, 7.44
(each 1H, m).
3-(3,4-Dimethoxyphenyl)-9-(2-furylmethyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one (13).
C H NO . Yield 78%, mp 141–142°C (propan-2-ol). PMR spectrum (300 MHz, CDCl , δ, ppm, J/Hz): 3.91, 3.93 (each
24 21
6
3
3
3H, s, OMe-3′, OMe-4′), 3.94 [2H, s, N(9)-CH ], 4.22 (2H, s, CH -10), 4.98 (2H, s, CH -8), 6.91 (1H, d, J = 8.4, H-5′), 6.93
2
2
2
494