8626
P. Thirupathi, S.S. Kim / Tetrahedron 66 (2010) 8623e8628
The products were characterized by 1H and 13C NMR data that
3H), 3.67 (s, 6H), 2.45e2.39 (m, 2H), 2.32 (s, 3H); 13C NMR
(100 MHz, CDCl3) 152.8, 142.9, 137.6, 136.8, 135.8, 133.2, 129.5,
are consistent with literature values. Melting point, HRMS-FAB, 1H,
and 13C NMR values for new products are given below.
d
129.0, 127.1, 126.3, 118.8, 103.5, 60.4, 57.7, 55.8, 41.7, 21.3; HRMS-FAB
(m/z) [MþH]þ calcd for C20H26NO5S 391.1453, found 391.1453.
4.2.1. Compound 5a. White solid, mp 75e76 ꢁC; IR (KBr): nmax 3261,
1458, 1314, 1159, 1088 cmꢂ1
;
1H NMR (400 MHz, CDCl3)
d
7.51 (d,
4.2.9. Compound 5i. White solid, mp 127 ꢁC; IR (KBr): nmax 3285,
J¼8.4 Hz, 2H), 7.14e7.01 (m, 7H), 5.50e5.43 (m, 1H), 5.11 (br s, 1H),
1518, 1362, 1148, 1064 cmꢂ1 1H NMR (400 MHz, CDCl3)
; d 8.00 (d,
4.99 (d, J¼14.0 Hz, 2H), 4.33 (q, J¼7.0 Hz, 1H), 2.46e2.36 (m, 2H),
J¼8.8 Hz, 2H), 7.55 (d, J¼8.4 Hz, 2H), 7.28 (d, J¼8.8 Hz, 2H), 7.14 (d,
J¼8.0 Hz, 2H), 5.60 (d, J¼6.2 Hz, 1H), 5.50e5.48 (m, 1H), 5.04 (d,
J¼5.5 Hz, 1H), 5.02 (d, J¼12.5 Hz, 1H), 4.44 (q, J¼7.0 Hz, 1H),
2.32 (s, 3H); 13C NMR (100 MHz, CDCl3)
d 143.0, 140.3, 137.4, 133.1,
129.2, 128.3, 127.3, 127.1, 126.5, 119.1, 57.2, 41.8, 21.4.5c,6g,l
2.44e2.39 (m, 2H), 2.35 (s, 3H); 13C NMR (100 MHz, CDCl3)
d: 147.9,
4.2.2. Compound 5b. White solid, mp 159e160 ꢁC; IR (KBr): nmax
146.9, 143.8, 131.9, 129.4, 127.5, 127.0, 123.4, 120.1, 56.6, 41.4, 21.3.6g
3261,1456,1314,1159,1076 cmꢂ1; 1H NMR (400 MHz, CDCl3)
d 7.53 (d,
J¼8.4 Hz, 2H), 7.13e7.07 (m, 4H), 6.98 (d, J¼8.0 Hz, 2H), 5.51e5.44 (m,
4.2.10. Compound 5j. White solid, mp 148e149 ꢁC; IR (KBr): nmax
2H), 5.03 (s, 1H), 5.00e4.98 (m, 1H), 4.32 (q, J¼7.0 Hz,1H), 2.43e2.36
3297, 2210, 1338, 1135, 1064 cmꢂ1; 1H NMR (400 MHz, CDCl3)
d 7.51
(m, 2H), 2.38 (s, 3H); 13C NMR (100 MHz, CDCl3)
d
143.2, 138.8, 137.2,
(d, J¼8.4 Hz, 2H), 7.39 (d, J¼7.8 Hz, 2H), 7.17 (d, J¼8.0 Hz, 2H), 7.10 (d,
J¼8.0 Hz, 2H), 5.65 (d, J¼6.6 Hz, 1H), 5.42e5.39 (m, 1H), 4.99 (d,
J¼4.7 Hz,1H), 4.97 (d, J¼11.7 Hz,1H), 4.35 (q, J¼7.0 Hz,1H), 2.37e2.33
132.9, 132.7, 129.2, 128.3, 128.0, 127.0, 119.2, 56.7, 41.5, 21.3.5c,6l
4.2.3. Compound 5c. Viscous mass; IR (KBr): nmax 3273, 1589, 1422,
(m, 2H), 2.34 (s, 3H); 13C NMR (100 MHz, CDCl3)
d: 145.9,143.5,136.9,
1291, 1148, 1088 cmꢂ1
;
1H NMR (400 MHz, CDCl3)
d
7.54 (d,
132.0, 129.3, 127.4, 127.0, 119.8, 118.5, 110.9, 56.8, 41.3, 21.3.
J¼8.4 Hz, 2H), 7.14 (d, J¼8.4 Hz, 2H), 7.09 (d, J¼6.0 Hz, 2H),
7.02e6.98 (m, 1H), 6.94 (s, 1H), 5.54e5.44 (m, 2H), 5.06 (s, 1H), 5.02
(d, J¼5.8 Hz, 1H), 4.34 (q, J¼7.0 Hz, 1H), 2.44e2.38 (m, 2H), 2.36 (s,
4.2.11. Compound 5k. White solid, mp 84e85 ꢁC; IR (KBr): nmax
3249, 2210, 1327, 1159, 1052 cmꢂ1; 1H NMR (400 MHz, CDCl3)
d 7.49
3H); 13C NMR (100 MHz, CDCl3)
d
143.2, 142.3, 137.1, 134.0, 132.6,
(d, J¼8.4 Hz, 2H), 7.39e7.34 (m, 2H), 7.27e7.22 (m, 2H), 7.10 (d,
J¼8.4 Hz, 2H), 5.60 (br s, 1H), 5.47e5.39 (m, 1H), 5.03e4.96 (m, 2H),
4.35 (q, J¼6.7 Hz, 1H), 2.40e2.35 (m, 2H), 2.36 (s, 3H); 13C NMR
129.5, 129.2, 127.3, 127.0, 126.8, 124.8, 119.4, 56.8, 41.5, 21.3; HRMS-
FAB (m/z) [MþH]þ calcd for C17H19ClNO2S 336.0825, found
336.0825.
(100 MHz, CDCl3)
d 143.5, 141.9, 137.0, 132.1, 131.2, 130.7, 130.2,
129.4, 129.0,126.9, 119.8,118.3,112.1, 56.6, 41.4, 21.3; HRMS-FAB (m/
4.2.4. Compound 5d. White solid, mp 113e114 ꢁC; IR (KBr): nmax
z): [MþH]þ calcd for C18H19N2O2S: 327.1167, found: 327.1165.
3261, 1446, 1327, 1159, 1086 cmꢂ1; 1H NMR (400 MHz, CDCl3)
d 7.60
(d, J¼8.4 Hz, 2H), 7.21e7.17 (m, 2H), 7.12 (d, J¼7.0 Hz, 2H), 7.08e7.05
(m, 2H), 5.58e5.44 (m, 2H), 5.03 (d, J¼15 Hz, 2H), 4.83 (q, J¼7.0 Hz,
1H), 2.48e2.38 (m, 2H), 2.34 (s, 3H); 13C NMR (100 MHz, CDCl3)
4.2.12. Compound 8a. White solid, mp 67 ꢁC; IR (KBr): nmax 3367,
1685, 1530, 1257, 1028 cmꢂ1; 1H NMR (400 MHz, CDCl3)
d
7.31e7.22
(m, 10H), 5.70e5.59 (m, 1H), 5.20 (br s, 1H), 5.10e5.01 (m, 4H), 4.79
d
143.1, 137.8, 136.8, 132.7, 131.9, 129.4, 129.2, 128.3, 128.2, 127.1,
(br s, 1H), 2.51 (s, 2H); 13C NMR (100 MHz, CDCl3)
d 155.7, 142.0,
126.7, 119.3, 54.0, 40.3, 21.4; HRMS-FAB (m/z) [MþH]þ calcd for
136.5, 133.8, 128.6, 128.5, 128.1, 127.3, 126.3, 118.4, 66.8, 54.6, 41.1.5g
C17H19ClNO2S 336.0825, found 336.0826.
4.2.13. Compound 8b. White solid, mp 63e64 ꢁC; IR (KBr): nmax
4.2.5. Compound 5e. White solid, mp 129e130 ꢁC; IR (KBr): nmax
3357, 1697, 1518, 1267, 1040 cmꢂ1; 1H NMR (400 MHz, CDCl3)
d 7.27
3249, 1446, 1327, 1159, 1064 cmꢂ1; 1H NMR (400 MHz, CDCl3)
d
7.52
(s, 5H), 7.11e7.07 (m, 5H), 5.68e5.58 (m, 1H), 5.32 (br s, 1H),
(d, J¼8.4 Hz, 2H), 7.25 (d, J¼8.4 Hz, 2H), 7.13 (d, J¼8.4 Hz, 2H), 6.93
(d, J¼8.4 Hz, 2H), 5.54e5.45 (m, 1H), 5.34 (d, J¼6.6 Hz, 1H), 5.05 (s,
1H), 5.02 (d, J¼8.4 Hz,1H), 4.32 (q, J¼7.0 Hz,1H), 2.43e2.38 (m, 2H),
5.07e4.98 (m, 4H), 4.74 (br s, 1H), 2.46 (s, 2H), 2.28 (s, 3H); 13C NMR
(100 MHz, CDCl3)
d 155.6, 138.9, 136.7, 136.4, 133.8, 129.1, 128.3,
127.9, 126.1, 118.1, 66.5, 54.2, 40.9, 20.9.11f
2.39 (s, 3H); 13C NMR (100 MHz, CDCl3)
d: 143.3, 139.3, 137.2, 132.6,
131.3, 129.3, 128.3, 127.0, 121.1, 119.4, 56.6, 41.5, 21.4; HRMS-FAB
4.2.14. Compound 8c. White solid, mp 51e52 ꢁC; IR (KBr): nmax
(m/z) [MþH]þ calcd for C17H19BrNO2S 380.0143, found 380.0137.
3344, 1673, 1541, 1267, 1028 cmꢂ1; 1H NMR (400 MHz, CDCl3)
d 7.35
(s, 5H), 7.25e7.18 (m, 5H), 5.80e5.70 (m, 1H), 5.23 (br s, 1H),
4.2.6. Compound 5f. White solid, mp 118e119 ꢁC; IR (KBr): nmax
5.17e5.04 (m, 5H), 2.52 (s, 2H), 2.43 (s, 3H); 13C NMR (100 MHz,
3261, 1446, 1314, 1159, 1088 cmꢂ1; 1H NMR (400 MHz, CDCl3)
d
7.55
CDCl3) d 155.7, 140.3, 136.5, 135.4, 134.0, 130.7, 128.5, 128.1, 127.2,
(d, J¼8.4 Hz, 2H), 7.14 (d, J¼8.7 Hz, 2H), 7.01e6.93 (m, 4H),
5.55e5.45 (m, 1H), 5.02 (dd, J¼12.0, 2.0 Hz, 3H), 4.31 (q, J¼7.0 Hz,
1H), 2.49e2.39 (m, 2H), 2.37 (s, 3H), 2.26 (s, 3H); 13C NMR
126.3, 125.1, 118.3, 66.8, 50.8, 40.3, 19.3.11h
4.2.15. Compound 8d. White solid, mp 69e70 ꢁC; IR (KBr): nmax
(100 MHz, CDCl3)
d
142.9, 137.5, 137.3, 137.0, 129.6, 129.2, 128.9,
3309, 1684, 1541, 1255, 1028 cmꢂ1; 1H NMR (400 MHz, CDCl3)
d 7.30
127.1, 126.4, 119.0, 56.9, 41.7, 21.4, 20.9.5c,6g,l
(s, 5H), 7.16 (d, J¼7.8 Hz, 2H), 6.83 (d, J¼8.4 Hz, 2H), 5.70e5.59 (m,
1H), 5.14 (br s, 1H), 5.10e5.00 (m, 4H), 4.72 (br s, 1H), 3.76 (s, 3H),
4.2.7. Compound 5g. White solid, mp 86e87 ꢁC; IR (KBr): nmax
2.49 (s, 2H); 13C NMR (100 MHz, CDCl3)
d 158.7, 155.6, 136.4, 133.8,
3261, 1530, 1314, 1159, 1028 cmꢂ1; 1H NMR (400 MHz, CDCl3)
d
7.52
128.4, 128.0, 127.3, 118.2, 113.8, 66.6, 55.1, 54.0, 40.9.5g
(d, J¼7.8 Hz, 2H), 7.09 (d, J¼8.0 Hz, 2H), 6.94 (d, J¼8.8 Hz, 2H), 6.64
(d, J¼8.4 Hz, 2H), 5.49e5.43 (m, 1H), 5.24 (br s, 1H), 4.99 (d,
J¼6.6 Hz, 2H), 4.27 (q, J¼7.0 Hz, 1H), 3.69 (s, 3H), 2.44e2.36 (m, 2H),
4.2.16. Compound 8e. White solid, mp 70 ꢁC; IR (KBr): nmax 3344,
1697, 1530, 1243, 1124 cmꢂ1; 1H NMR (400 MHz, CDCl3)
d
7.35e7.25
(m, 5H), 6.46 (s, 2H), 5.73e5.62 (m, 1H), 5.18e5.08 (m, 6H), 4.75 (br
s, 1H), 3.81 (s, 9H), 2.51 (s, 2H); 13C NMR (100 MHz, CDCl3)
156.3,
2.32 (s, 3H); 13C NMR (100 MHz, CDCl3)
d: 158.7, 142.8, 137.5, 133.3,
132.4, 131.9, 129.2, 127.7, 127.0, 118.7, 113.6, 56.8, 55.1, 41.7, 21.3.5c
d
153.8, 138.3, 137.6, 136.9, 134.3, 129.0, 128.6, 119.0, 103.7, 67.4, 61.3,
4.2.8. Compound 5h. White solid, mp 67e68 ꢁC; IR (KBr): nmax
56.6, 55.3, 41.7.11f
3257, 1458, 1314, 1159, 1111 cmꢂ1; 1H NMR (400 MHz, CDCl3)
d 7.50
(d, J¼7.8 Hz, 2H), 7.08 (d, J¼7.8 Hz, 2H), 6.21 (s, 2H), 5.58e5.52 (m,
4.2.17. Compound 8f. White solid, mp 45e46 ꢁC; IR (KBr): nmax
2H), 5.05 (d, J¼8.4 Hz,1H), 5.02 (s,1H), 4.30 (q, J¼7.0 Hz,1H), 3.72 (s,
3311, 1679, 1534, 1255, 1056 cmꢂ1 1H NMR (400 MHz, CDCl3)
;