Chemistry of Heterocyclic Compounds 2020, 56(10), 1283–1291
3
(6h). Yield 1.06 g (87%), yellow powder, mp 203–205°C.
IR spectrum, ν, cm–1: 1745, 1739, 1698, 1652, 1583, 1468,
1386, 1295. 1H NMR spectrum, δ, ppm (J, Hz): 1.15 (3H, t,
3JHH = 7.4, OCH2CH3); 1.25 (3H, t, 3JHH = 7.4, OCH2CH3);
1.34 (3H, t, 3JHH = 7.5, NCH2CH3); 1.78 (3H, s, CH3); 2.14
(3H, s, CH3); 2.45–2.58 (2H, m, NCH23CH3); 3.72 (3H, s,
3JHP = 11.7, CH3OP); 3.95 (3H, d, JHP = 11.7, CH3OP);
3 3
4.72 (1H, dd, JHH = 10.2, JHP = 8.7, PCCH); 4.83 (1H, d,
2JHH = 3.8, C=CH); 5.16 (1H, d, JHH = 3.8, C=CH); 6.28
2
3
(1H, s, NH); 7.02 (1H, d, JHH = 7.8, H Ar); 7.24 (1H, d,
3JHH = 7.8, H Ar); 7.45 (1H, s, H Ar); 7.58 (1H, s, H Ar);
7.95 (1H, s, H Ar). 13C NMR spectrum, δ, ppm (J, Hz):
18.6; 21.2; 25.4; 34.5; 42.5 (d, J = 9.5); 46.4 (d, J = 144.7);
51.3 (d, J = 8.6); 52.5 (d, J = 8.6); 53.2; 76.5; 105.3; 113.4;
114.3; 115.3; 121.6; 122.5; 122.7; 123.4; 124.4; 127.6;
133.7; 137.8; 142.5. 31P NMR spectrum, δ, ppm: 19.8.
Mass spectrum, m/z (Irel, %): 582 [M]+ (10), 551 (86), 31
(100). Found, %: C 59.92; H 5.52; N 4.97. C29H31N2O9P.
Calculated, %: C 59.79; H 5.36; N 4.81.
2
C(O)OCH3); 3.84 (1H, dd, JHP = 19.4, JHH = 11.2, PCH);
3.95–4.09 (2H, m, OCH2CH3); 4.15–4.26 (2H, m,
OCH2CH3); 4.65 (1H, dd, 3JHH = 11.2, 3JHP = 10.5, PCCH);
2
2
4.84 (1H, d, JHH = 5.8, C=CH); 5.03 (1H, d, JHH = 5.8,
C=CH); 6.32 (1H, s, NH); 7.02 (1H, d, 3JHH = 7.6, H Ar);
3
3
7.15 (1H, t, JHH = 7.6, H Ar); 7.32 (1H, t, JHH = 7.5,
H Ar); 7.46 (1H, s, H Ar); 7.58 (1H, s, H Ar); 7.89 (1H, d,
3JHH = 7.6, H Ar). 13C NMR spectrum, δ, ppm (J, Hz): 14.2;
14.8 (d, J = 9.4); 15.6 (d, J = 9.4); 18.6; 25.4; 40.2; 41.6 (d,
J = 11.2); 47.5 (d, J = 155.8); 51.6; 61.8 (d, J = 9.8); 62.6
(d, J = 9.8); 76.3; 106.4; 113.6; 114.3; 114.8; 121.4; 122.3;
123.2; 124.8; 125.8; 128.2; 133.4; 137.6; 143.2; 151.6;
152.8; 154.3; 160.8; 161.6 (d, J = 8.3); 169.4 (d, J = 22.3).
31P NMR spectrum, δ, ppm: 23.4. Mass spectrum, m/z (Irel, %):
610 [M]+ (10), 565 (54), 45 (100), 31 (100). Found, %:
C 60.63; H 5.92; N 4.76. C31H35N2O9P. Calculated, %:
C 60.48; H 5.78; N 4.59.
Methyl (8R,9R)-8-(dimethoxyphosphoryl)-5-(3-ethyl-
2,6-dimethyl-4-oxo-1,2,3,4-tetrahydro-2-quinazolinyl)-
2-isopropenyl-7-oxo-8,9-dihydro-7H-furo[2,3-f]chromene-
9-carboxylate (6k). Yield 1.07 g (90%), yellow powder,
mp 207–209°C. IR spectrum, ν, cm–1: 1742, 1736, 1698, 1637,
1
1589, 1482, 1387, 1295. H NMR spectrum, δ, ppm (J, Hz):
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1.27 (3H, t, JHH = 7.4, CH2CH3); 1.75 (3H, s, CH3); 2.16
(3H, s, CH3); 2.35 (3H, s, CH3); 2.76–2.85 (1H, m, CH3CH2);
3.13–3.27 (1H, m, CH3CH2); 3.78 (3H, s, C(O)OCH3); 3.83
2
3
(1H, dd, JHP = 19.7, JHH = 11.5, PCH); 3.92 (3H, d,
3
Ethyl (8R,9R)-5-[3-(tert-butyl)-2-methyl-4-oxo-1,2,3,4-
tetrahydro-2-quinazolinyl]-8-(diphenoxyphosphoryl)-
2-isopropenyl-7-oxo-8,9-dihydro-7H-furo[2,3-f]chromene-
9-carboxylate (6i). Yield 1.09 g (73%), pale-yellow
powder, mp 221–223°C. IR spectrum, ν, cm–1: 1742, 1738,
3JHP = 11.5, CH3OP); 3.96 (3H, d, JHP = 11.5, CH3OP);
4.75 (1H, dd, 3JHH = 11.6, 3JHP = 10.3, PCCH); 4.85 (1H, d,
2JHH = 4.7, C=CH); 5.26 (1H, d, JHH = 4.7, C=CH); 6.22
2
(1H, s, NH); 7.12 (1H, d, 3JHH = 7.6, H Ar); 7.28 (1H, d,
3JHH = 7.6, H Ar); 7.49 (1H, s, H Ar); 7.56 (1H, s, H Ar);
7.93 (1H, s, H Ar). 13C NMR spectrum, δ, ppm (J, Hz): 14.2;
1
1697, 1675, 1587, 1487, 1387, 1295. H NMR spectrum,
δ, ppm (J, Hz): 1.23 (9H, s, (CH3)3C); 1.28 (3H, t, 3JHH = 7.4,
18.6, 22.4; 25.6; 40.5; 42.7 (d, JPC = 9.8); 45.9 (d,
2
OCH2CH3); 1.67 (3H, s, CH3); 2.15 (3H, s, CH3); 4.12 (2H,
1JPC = 145.3); 51.4 (d, J = 9.3); 52.6 (d, J = 9.3); 53.5; 76.7;
106.3; 113.7; 114.2; 114.7; 121.9; 122.6; 123.2; 123.8; 124.5;
127.5; 131.6; 137.4; 142.3; 151.4; 152.2; 154.7; 160.7;
161.6 (d, J = 6.8); 168.4 (d, J = 22.5). 31P NMR spectrum,
δ, ppm: 21.2. Mass spectrum, m/z (Irel, %): 596 [M]+ (15),
565 (84), 31 (100). Found, %: C 60.52; H 5.73; N 4.85.
C30H33N2O9P. Calculated, %: C 60.40; H 5.58; N 4.70.
Methyl (8R,9R)-5-[3-(tert-butyl)-2-methyl-6-nitro-4-oxo-
1,2,3,4-tetrahydro-2-quinazolinyl]-8-(dimethoxyphosphoryl)-
2-isopropenyl-7-oxo-8,9-dihydro-7H-furo[2,3-f]chromene-
9-carboxylate (6l). Yield 1.11 g (85%), yellow powder,
mp 222–224°C. IR spectrum, ν, cm–1: 1739, 1735, 1685,
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2
q, JHH = 7.4, OCH2CH3); 4.27 (1H, dd, JHP = 19.8,
3JHH = 12.0, PCH); 4.90 (1H, dd, JHH = 12.0, JHP = 10.7,
3
3
2
PCCH); 4.97 (1H, d, JHH = 4.2, C=CH); 5.28 (1H, d,
2JHH = 4.2, C=CH); 6.25 (1H, s, NH); 6.86 (1H, d,
3JHH = 7.6, H Ar); 7.14 (2H, d, 3JHH = 7.6, H Ar); 7.18 (2H,
3
3
d, JHH = 7.5, H Ar); 7.22 (1H, t, JHH = 7.5, H Ar); 7.28
3
3
(1H, t, JHH = 7.5, H Ar); 7.33 (1H, t, JHH = 7.5, H Ar);
3
3
7.42 (1H, t, JHH = 7.6, H Ar); 7.48 (2H, t, JHH = 7.5,
3
H Ar); 7.52 (2H, t, JHH = 7.5, H Ar); 7.63 (1H, s, H Ar);
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7.68 (1H, s, H Ar); 8.12 (1H, d, JHH = 7.6, H Ar).
13C NMR spectrum, δ, ppm (J, Hz): 14.2; 18.5; 26.8; 31.2;
38.2 (d, J = 11.4); 41.2 (d, J = 156.7); 60.3; 62.3; 77.2;
113.5; 114.3; 115.2; 116.3; 117.3; 120.7 (d, J = 22.8); 121.5
(d, J = 22.8); 123.4; 123.8; 125.3; 125.8; 126.3; 126.8; 127.6;
128.2; 128.6; 134.2; 137.6; 142.8; 151.6 (d, J = 10.8);
152.3 (d, J = 10.8); 152.6; 153.6; 154.2; 159.6; 161.2 (d,
J = 7.8); 168.4 (d, J = 21.7). 31P NMR spectrum, δ, ppm:
22.6. Mass spectrum, m/z (Irel, %): 748 [M]+ (10), 691 (64), 57
(100). Found, %: C 67.53; H 5.73; N 3.92. C42H41N2O9P.
Calculated, %: C 67.37; H 5.52; N 3.74.
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1656, 1578, 1486, 1383, 1292. H NMR spectrum, δ, ppm
(J, Hz): 1.18 (9H, s, C(CH3)3); 1.65 (3H, s, CH3); 2.23 (3H,
s, CH3); 3.75 (3H, s, C(O)OCH3); 3.87 (1H, dd, 2JHP = 21.2,
3JHH = 12.3, PCH); 3.92 (3H, d, JHP = 12.3, CH3OP); 3.96
3
3
2
(3H, d, JHP = 12.3, CH3OP); 4.75 (1H, d, JHH = 5.2,
C=CH); 4.88 (1H, dd, 3JHH = 11.7, 3JHP = 9.5, PCCH); 5.18
2
(1H, d, JHH = 5.2, C=CH); 6.27 (1H, s, NH); 7.15 (1H, d,
3JHH = 7.6, H Ar); 7.32 (1H , d, 3JHH = 7.6, H Ar); 7.46 (1H,
s, H Ar); 7.58 (1H, s, H Ar); 8.37 (1H, s, H Ar). 13C NMR
spectrum, δ, ppm (J, Hz): 18.5; 27.6; 31.6; 43.2 (d, J = 10.5);
47.6 (d, J = 148.4); 51.6 (d, J = 9.2); 52.4 (d, J = 9.2); 53.2;
62.5; 77.8; 113.6; 114.5; 114.9; 115.5; 116.7; 123.4; 123.9;
124.6; 127.8; 134.6; 137.5; 138.8; 142.3; 152.7; 153.2;
155.3; 161.2; 161.7 (d, J = 6.7); 169.5 (d, J = 21.4).
31P NMR spectrum, δ, ppm: 22.3. Mass spectrum, m/z (Irel, %):
655 [M]+ (10), 598 (78), 31 (100). Found, %: C 56.92;
H 5.43; N 6.67. C31H34N3O11P. Calculated, %: C 56.79;
H 5.23; N 6.41.
Methyl (8R,9R)-8-(dimethoxyphosphoryl)-5-(2,3,6-tri-
methyl-4-oxo-1,2,3,4-tetrahydro-2-quinazolinyl)-2-iso-
propenyl-7-oxo-8,9-dihydro-7H-furo[2,3-f]chromene-
9-carboxylate (6j). Yield 1.07 g (92%), yellow powder,
mp 201–203°C. IR spectrum, ν, cm–1: 1743, 1737, 1697,
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1648, 1574, 1478, 1364, 1285. H NMR spectrum, δ, ppm
(J, Hz): 1.65 (3H, s, CH3); 2.17 (3H, s, CH3); 2.36 (3H, s,
CH3); 2.63 (3H, s, CH33); 3.75 (3H, s, C(O)OCH3); 3.83
2
(1H, dd, JHP = 19.5, JHH = 11.7, PCH); 3.87 (3H, d,
1288