S.T. Kadam et al. / Tetrahedron 65 (2009) 10383–10389
10387
5.98 (s, 1H), 3.91 (s, 3H), 3.82 (s, 3H), 3.51 (s, 3H), 2.35 (s, 3H); 13C
NMR (50 MHz, CDCl3) : 151.6, 149.8, 144.0, 143.0, 135.9, 133.5,
113.3, 113.1, 109.8, 96.8, 65.7, 56.5, 56.2, 55.8, 55.1, 16.1; HRMS-EI
d
(m/z): [M]þ calcd for C24H26O6S: 442.1450, found: 442.1460.
129.9, 128.9, 128.8, 128.5, 128.2, 113.1, 112.9, 96.8, 66.3, 56.5, 56.3,
55.9, 21.5; HRMS-EI (m/z): [M]þ calcd for C23H24O5S: 412.1344,
found: 412.1343.
4.2.11. Compound 10h. White solid, mp 156 ꢀC; 1H NMR (400 MHz,
CDCl3)
6.77 (s, 1H), 6.29 (s, 1H), 5.87 (s, 1H), 3.88 (s, 3H), 3.80 (s, 3H), 3.78
(s, 9H), 3.47 (s, 3H), 2.33 (s, 3H); 13C NMR (50 MHz, CDCl3)
: 153.0,
d: 7.55 (s, 1H), 7.49 (d, J¼8.0 Hz, 2H), 7.13 (d, J¼8.4 Hz, 2H),
4.2.4. Compound 8d. White solid, mp 110–111 ꢀC; 1H NMR
d
(400 MHz, CDCl3)
d
: 8.00 (d, J¼8.0 Hz, 1H), 7.64 (d, J¼8.5 Hz, 2H),
151.7, 150.0, 144.1, 143.1, 135.9, 129.0, 128.9, 128.8, 113.2, 112.7, 107.3,
96.9, 66.2, 60.8, 56.6, 56.3, 56.0, 56.0, 21.5; HRMS-EI (m/z): [M]þ
calcd for C26H30O8S: 502.1661, found: 502.1661.
7.56 (d, J¼8.5 Hz, 2H), 7.36–7.33 (m, 3H), 7.19 (d, J¼8.0 Hz, 2H), 6.62
(d, J¼8.5 Hz, 1H), 6.32 (s, 1H), 6.03 (s, 1H), 3.82 (s, 3H), 3.54 (s, 3H),
2.40 (s, 3H); 13C NMR (50 MHz, CDCl3)
d: 160.9, 157.9, 144.1, 136.0,
133.7, 130.8, 130.2, 129.0, 128.5, 128.2, 114.3, 104.7, 98.3, 66.4, 55.4,
55.3, 21.6; HRMS-EI (m/z): [M]þ calcd for C22H22O4S: 382.1239,
found: 382.1263.
4.2.12. Compound 10i. White solid, mp 147 ꢀC; 1H NMR (400 MHz,
CDCl3)
d
: 7.47 (d, J¼8.0 Hz, 2H), 7.44 (s, 1H), 7.26 (d, J¼5.1 Hz, 1H),
7.20 (d, J¼4.4 Hz, 1H), 7.11 (d, J¼8.0 Hz, 2H), 6.95 (dd, J¼5.1, 4.4 Hz,
1H), 6.28 (s, 1H), 6.23 (s, 1H), 3.86 (s, 3H), 3.81 (s, 3H), 3.49 (s, 3H),
4.2.5. Compound 10b. White solid, mp 122–123 ꢀC; 1H NMR
2.33 (s, 3H); 13C NMR (50 MHz, CDCl3)
d: 151.6, 150.1, 144.1, 142.9,
(400 MHz, CDCl3)
d
: 7.57 (s, 1H), 7.51 (d, J¼8.4 Hz, 2H), 7.45 (d,
134.9, 134.4, 129.4, 128.9, 128.8, 126.6, 124.5, 113.1, 112.1, 96.6, 62.2,
56.8, 56.3, 55.8, 21.3; HRMS-EI (m/z): [M]þ calcd for C21H22O5S2:
418.0909, found: 418.0915.
J¼8.0 Hz, 2H), 7.14 (d, J¼8.0 Hz, 2H), 7.12 (d, J¼8.4 Hz, 2H), 6.31
(s, 1H), 5.95 (s, 1H), 3.91 (s, 3H), 3.82 (s, 3H), 3.50 (s, 3H), 2.36
(s, 3H), 2.31 (s, 3H); 13C NMR (50 MHz, CDCl3)
d: 151.6, 149.8, 143.9,
143.1, 138.2, 136.1, 129.9, 129.3, 129.0, 128.9, 113.3, 113.2, 96.9, 66.1,
56.6, 56.4, 56.0, 21.6, 21.1; HRMS-EI (m/z): [M]þ calcd for
C24H26O5S: 426.1501, found: 426.1511.
4.2.13. Compound 10j. White solid, mp 173 ꢀC; 1H NMR (400 MHz,
CDCl3)
d
: 7.48 (d, J¼8.0 Hz, 2H), 7.42 (s, 1H), 7.17 (d, J¼8.0 Hz, 2H),
6.53 (d, J¼3.4 Hz, 1H), 6.37–6.36 (m, 1H), 6.34 (s, 1H), 6.12 (s, 1H),
3.87 (s, 3H), 3.85 (s, 3H), 3.55 (s, 3H), 2.38 (s, 3H); 13C NMR (50 MHz,
4.2.6. Compound 10c. White solid, mp 143.0 ꢀC; 1H NMR
CDCl3) d: 151.9, 150.4, 146.2, 144.2, 143.4, 143.3, 135.2, 129.1, 129.0,
(400 MHz, CDCl3)
d
: 7.58 (s,1H), 7.52–7.48 (m, 4H), 7.14 (d, J¼8.0 Hz,
114.0, 111.8, 110.8, 110.4, 96.7, 61.3, 56.5, 56.4, 56.0, 21.6; HRMS-EI
2H), 6.84 (d, J¼8.6 Hz, 2H), 6.32 (s, 1H), 5.93 (s, 1H), 3.92 (s, 3H),
(m/z): [M]þ calcd for C21H22O6S: 402.1137, found: 402.1141.
3.82 (s, 3H), 3.76 (s, 3H), 3.51 (s, 3H), 2.35 (s, 3H); 13C NMR (50 MHz,
CDCl3)
d
: 159.6, 151.6, 149.8, 144.0, 143.1, 136.0, 131.3, 129.0, 128.8,
4.2.14. Compound 10k. White solid, mp 146–147 ꢀC; 1H NMR
125.3, 114.0, 113.3, 113.1, 97.0, 65.8, 56.6, 56.5, 56.0, 55.2, 21.5;
HRMS-EI (m/z): [M]þ calcd for C24H26O6S: 442.1450, found:
442.1460.
(400 MHz, CDCl3)
d
: 8.36 (d, J¼8.6 Hz, 1H), 7.64 (d, J¼8.2 Hz, 2H),
7.62 (s, 1H), 7.46 (t, J¼8.6 Hz, 1H), 7.41 (d, J¼7.6 Hz, 1H), 7.33 (t,
J¼8.6 Hz,1H), 7.29 (d, J¼8.2 Hz, 2H), 6.73 (s,1H), 6.47 (s, 1H), 4.02 (s,
3H), 3.95 (s, 3H), 3.62 (s, 3H), 2.49 (s, 3H); 13C NMR (50 MHz, CDCl3)
4.2.7. Compound 10d. Yellow solid; 1H NMR (400 MHz, CDCl3)
d:
d: 152.1, 150.0, 144.2, 142.8, 135.7, 135.1, 131.9, 130.4, 129.5, 129.2,
7.65 (d, J¼8.4 Hz, 2H), 7.56 (d, J¼8.4 Hz, 2H), 7.46 (d, J¼8.0 Hz, 2H),
7.44 (s, 1H), 7.13 (d, J¼8.4 Hz, 2H), 6.27 (s, 1H), 5.96 (s, 1H), 3.86
(s, 3H), 3.79 (s, 3H), 3.46 (s, 3H), 2.33 (s, 3H); 13C NMR (50 MHz,
128.9, 128.8, 126.7, 113.4, 111.9, 96.6, 61.9, 56.4, 56.1, 55.7, 21.3;
HRMS-EI (m/z): [M]þ calcd for C23H23ClO5S: 446.0955, found:
446.0955.
CDCl3) d: 151.6, 150.3, 144.5, 143.1, 138.9, 135.3, 132.1, 130.6, 129.1,
128.7, 118.3, 112.8, 111.9, 111.5, 96.7, 66.9, 56.6, 56.1, 55.9, 21.5; EI
4.2.15. Compound 10l. White solid, mp 157–158 ꢀC; 1H NMR
(m/z): [M]þ 437, 283, 282, 266.
(400 MHz, CDCl3)
J¼8.5 Hz, 2H), 6.37 (s, 1H), 5.99 (s, 1H), 3.97 (s, 3H), 3.88 (s, 3H), 3.56
(s, 3H), 2.42 (s, 3H); 13C NMR (50 MHz, CDCl3)
: 151.6, 150.1, 144.3,
d: 7.57–7.54 (m, 5H), 7.32 (s, 2H), 7.22 (d,
4.2.8. Compound 10e. Yellow solid, mp 148 ꢀC; 1H NMR (400 MHz,
d
CDCl3)
d
: 8.09 (d, J¼8.6 Hz, 2H), 7.73 (d, J¼8.2 Hz, 2H), 7.46 (d,
143.1,135.6,135.5,134.3, 130.1,129.7,129.1,128.8, 128.4,128.0,112.9,
112.2, 96.7, 65.7, 56.6, 56.3, 55.9, 21.5; HRMS-EI (m/z): [M]þ calcd for
C23H23ClO5S: 446.0955, found: 446.0949.
J¼8.6 Hz, 2H), 7.43 (s, 1H), 7.11 (d, J¼8.2 Hz, 2H), 6.28 (s, 1H), 6.04
(s, 1H), 3.84 (s, 3H), 3.76 (s, 3H), 3.44 (s, 3H), 2.30 (s, 3H); 13C NMR
(50 MHz, CDCl3) d: 151.5, 150.2, 147.2, 144.5, 142.9, 140.8, 135.0,
130.7, 129.0, 128.5, 123.3, 112.6, 111.2, 96.5, 65.5, 56.4, 56.0, 55.7,
21.3; HRMS-EI (m/z): [M]þ calcd for C23H23NO7S: 457.1195, found:
457.1189.
4.2.16. Compound 10m. White solid, mp 137 ꢀC; 1H NMR
(400 MHz, CDCl3)
(d, J¼8.5 Hz, 2H), 6.29 (s, 1H), 5.93 (s, 1H), 3.88 (s, 3H), 3.79 (s, 3H),
3.46 (s, 3H), 2.32 (s, 3H); 13C NMR (50 MHz, CDCl3)
: 151.5, 149.9,
d
: 7.50–7.47 (m, 5H), 7.25 (d, J¼8.5 Hz, 2H), 7.17
d
4.2.9. Compound 10f. White solid, mp 146–147 ꢀC; 1H NMR
144.1,143.0,135.5,134.1,132.0,131.2,128.9,128.6,128.5,112.9,112.3,
96.7, 65.5, 56.5, 56.1, 55.8, 21.3; HRMS-EI (m/z): [M]þ calcd for
C23H23ClO5S: 446.0955, found: 446.0955.
(400 MHz, CDCl3)
d
: 7.55 (s, 1H), 7.47 (d, J¼8.2 Hz, 2H), 7.37 (d,
J¼8.0 Hz, 1H), 7.22 (s, 1H), 7.08 (d, J¼8.2 Hz, 2H), 6.71 (d, J¼8.0 Hz,
1H), 6.26 (s, 1H), 5.86 (s, 1H), 3.87 (s, 3H), 3.76 (s, 3H), 3.73 (s, 3H),
3.44 (s, 3H), 2.29 (s, 3H), 2.12 (s, 3H); 13C NMR (50 MHz, CDCl3)
d:
4.2.17. Compound 10n. White solid, mp 123–124 ꢀC; 1H NMR
157.6, 151.4, 149.6, 143.7, 142.9, 135.9, 132.3, 128. 8, 128.7, 128.3,
126.5, 124.5, 113.2, 113.1, 109.7, 96.8, 65.6, 56.5, 56.2, 55.8, 55.1, 21.3,
16.1; HRMS-EI (m/z): [M]þ calcd for C25H28O6S: 456.1607, found:
456.1597.
(400 MHz, CDCl3)
d
: 7.43 (d, J¼8.5 Hz, 2H), 7.36 (s, 1H), 7.28–7.23
(m, 2H), 7.20–7.13 (m, 3H), 7.07 (d, J¼8.5 Hz, 2H), 6.99 (s, 1H), 6.30
(s,1H), 4.79 (d, J¼6.5 Hz,1H), 3.87 (s, 6H), 3.37 (s, 3H), 2.80–2.77 (m,
1H), 2.68–2.43 (m, 1H), 2.42–2.38 (m, 1H), 2.37 (s, 3H); 13C NMR
(50 MHz, CDCl3) d: 151.9, 149.1, 143.0, 142.3, 139.6, 134.3, 128.0,
4.2.10. Compound 10g. White solid, mp 131–133 ꢀC; 1H NMR
127.8, 127.5, 127.5, 127.4, 127.2, 127.1, 125.2, 110.5, 95.5, 65.7, 55.6,
55.0, 54.9, 31.7, 27.9, 20.6; HRMS-EI (m/z): [M]þ calcd for
C25H28O5S: 440.1657, found: 440.1656.
(400 MHz, CDCl3)
d
: 7.62 (d, J¼8.4 Hz, 2H), 7.57 (s, 1H), 7.49–7.42
(m, 2H), 7.33 (t, J¼7.6 Hz, 2H), 7.27 (s, 1H), 6.76 (d, J¼8.4 Hz, 1H),
6.27 (s, 1H), 5.92 (s, 1H), 3.91 (s, 3H), 3.80 (s, 3H), 3.77 (s, 3H), 3.45
(s, 3H), 2.16 (s, 3H), 2.12 (s, 3H); 13C NMR (50 MHz, CDCl3)
d: 157.8,
4.2.18. Compound 10o. White solid, mp 117 ꢀC; 1H NMR
151.5, 149.8, 143.0, 138.9, 132.9, 128.7, 128.4, 128.2, 126.7, 124.3,
(400 MHz, CDCl3)
d
: 7.35 (d, J¼8.4 Hz, 2H), 7.32 (s, 1H), 7.31 (s, 1H),