M. Kidwai et al. · Reaction of Coumarin Derivatives with Nucleophiles in Aqueous Medium
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jol): ν = 1605, 1660, 3440 cm−1. – 1H NMR (300 MHz, 4-(4-Methoxyphenyl)-1,2,3,4-tetrahydrobenzopyrano[4,3-
CDCl3, TMS): δ = 2.47 (d, 1 H, J = 9.6 Hz), 4.81 (d, 1 H, d]pyrimidine-2-thioxo-5-one (11a)
J = 8.2 Hz), 6.80 – 7.65 (m, 9 H, Ar-H), 11.25 (s, 1 H, NH). –
M. p. 234 – 236 ◦C (234 ◦C [25]). – C18H14O3N2S: calcd.
C 63.85, H 4.14, N 8.28, S 9.46; found C 63.89, H 4.12,
N 8.25, S 9.45. – IR (nujol): ν = 1675, 3455 cm−1. –
1H NMR (300 MHz, CDCl3, TMS): δ = 3.84 (s, 3 H,
OCH3), 6.07 (s, 1 H), 6.83 – 7.53 (m, 8 H, Ar-H), 11.50 (brs,
2 H, 2NH). – MS: m/z (%) = 338.6 (100) [M]+.
MS: m/z (%) = 264.0 (100) [M]+.
4-(4-Methoxyphenyl)-1,2,3,4-tetrahydrobenzopyrano[4,3-
d]pyrimidine-2,5-dione (10a)
M. p. 242 ◦C (240 ◦C [25]). – C18H14O4N2: calcd.
C 67.08, H 4.34, N 8.69; found C 67.05, H 4.31, N 8.73. –
IR (nujol): ν = 1660, 3450 cm−1. – 1H NMR (300 MHz,
CDCl3, TMS): δ = 3.86 (s, 3 H, OCH3), 6.12 (s, 1 H), 6.85 –
7.55 (m, 8 H, Ar-H), 11.53 (brs, 2 H, 2NH). – MS: m/z (%) =
321.8 (100) [M]+.
4-(4-Chlorophenyl)-1,2,3,4-tetrahydrobenzopyrano[4,3-d]-
pyrimidine-2-thioxo-5-one (11b)
M. p. 187 – 189 ◦C (188 – 190 ◦C [26]).
–
C17H11O2N2ClS: calcd. C 59.56, H 3.21, N 8.17, S 9.34;
found C 59.54, H 3.20, N 8.1, S 9.35. – IR (nujol): ν = 1680,
3450 cm−1. – 1H NMR (300 MHz, CDCl3, TMS): δ = 6.08
(s, 1 H), 6.86 – 7.82 (m, 8 H, Ar-H), 11.50 (brs, 2 H, 2NH). –
MS: m/z (%) = 342.0 (100) [M]+.
4-(4-Chlorophenyl)-1,2,3,4-tetrahydrobenzopyrano[4,3-d]-
pyrimidine-2,5-dione (10b)
M. p. 161 – 163 ◦C (162 – 164 ◦C [26]). – C17H11O3N2Cl:
calcd. C 62.48, H 3.36, N 8.57; found C 62.49, H 3.36,
N 8.54. – IR (nujol) : ν = 1670, 3450 cm−1. – 1H NMR
(300 MHz, CDCl3, TMS): δ = 6.11 (s, 1 H), 6.89 – 7.65 (m,
8 H, Ar-H), 11.52 (brs, 2 H, 2NH). – MS: m/z (%) = 326.0
(100) [M]+.
4-(Thiophen-2-yl)-1,2,3,4-tetrahydrobenzopyrano[4,3-d]-
pyrimidine-2-thioxo-5-one (11c)
M. p. 245 – 247 ◦C. – C15H10N2O2S: calcd. C 57.32,
H 3.18, N 8.91, S 20.38; found C 57.31, H 3.15, N 8.71,
S 20.34. – IR (nujol): ν = 1680, 3455 cm−1. – 1H NMR
(300 MHz, CDCl3, TMS): δ = 6.08 (s, 1 H), 6.77 – 7.65 (m,
7 H, Ar-H + thienyl), 11.40 (brs, 2 H, 2NH). – MS: m/z (%) =
314.7 (100) [M]+.
4-(Thiophen-2-yl)-1,2,3,4-tetrahydrobenzopyrano[4,3-d]-
pyrimidine-2,5-dione (10c)
M. p. 168 – 170 ◦C. – C15H10N2O3S: calcd. C 60.40,
H 3.35, N 9.39, S 10.73; found C 60.4, H 3.37, N 9.36,
S 10.75. – IR (nujol): ν = 1675, 3440 cm−1. – 1H NMR
(300 MHz, CDCl3, TMS): δ = 6.14 (s, 1 H), 6.79 – 7.65 (m,
7 H, Ar-H + thienyl), 11.55 (brs, 2 H, 2NH). – 13C NMR
(75.6 Hz, CDCl3, TMS): δ = 127.6, 126.3, 129.5, 122.3,
153.8, 171.0, 104.5, 54.8, 127.5, 129.5, 126.4, 143.5, 162.0,
149.2, 140.8. – MS: m/z (%) = 297.8 (100) [M]+.
4-Phenyl-1,2,3,4-tetrahydrobenzopyrano[4,3-d]pyrimidine-
2-thioxo-5-one (11d)
M. p. 188 – 189 ◦C (188 ◦C [25]). – C17H12O2N2S: calcd.
C 62.23, H 3.89, N 9.09, S 10.38; found C 62.21, H 3.87,
N 9.07, S 10.39. – IR (nujol): ν = 1670, 3445 cm−1. –
1H NMR (300 MHz, CDCl3, TMS): δ = 6.05 (s, 1 H), 6.79 –
7.68 (m, 9 H, Ar-H), 11.48 (brs, 2 H, 2NH). – 13C NMR
(75.6 MHz, CDCl3, TMS): δ = 128.6, 125.0, 130.1, 122.3,
152.8, 171.0, 101.9, 58.2, 129.1, 130.3, 128.5, 130.1, 128.9,
144.4, 184.2, 163.2, 129.8. – MS: m/z (%) = 308.0 (100)
[M]+.
4-Phenyl-1,2,3,4-tetrahydrobenzopyrano[4,3-d]pyrimidine-
2,5-dione (10d)
◦
M. p. 162 – 163 ◦C (162 C [25]). – C17H12O3N2: calcd.
C 69.86, H 4.10, N 9.58; found C 69.85, H 4.14, N 9.56. –
IR (nujol): ν = 1680, 3445 cm−1. – 1H NMR (300 MHz,
CDCl3, TMS): δ = 6.12 (s, 1 H), 6.79 – 7.65 (m, 9 H, Ar-H),
11.53 (brs, 2 H, 2NH). – MS: m/z (%) = 292.0 (100) [M]+.
Acknowledgement
The authors are thankful to CSIR, New Delhi, for their
financial assistance.
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