ORDER
REPRINTS
3-(Aryloxyacetyl)-2,3-dihydrothieno[2,3-b][1]benzothiopyrans
2165
1H, OCH2), 6.93–7.53 (m, 7H, ArH), 8.39 (d, J ¼ 8.51 Hz, 1H, ArH); m/
z ¼ 390, 388 (Mþ); Anal. calcd for C19H13ClO3S2: C, 58.76; H, 3.35;
Found C, 58.57; H, 3.52%.
Compound 5c. Yield (67%); white solid; m.p. 1388C; lmax (nm) 223
(log 1 ¼ 3.61), 230 (log 1 ¼ 3.74), 269 (log 1 ¼ 3.93); n
(cm21) 1710,
¯
max
1580, 1560, 1220; dH (500 MHz) 2.29 (s, 3H, CH3), 3.63 (dd, J ¼ 9.10,
11.22 Hz, 1H, SCH2), 3.70 (dd, J ¼ 7.20, 11.22 Hz, 1H, SCH2), 5.01
(dd, J ¼ 7.20, 9.10 Hz, 1H, CH), 4.87 (d, J ¼ 15.20 Hz, 1H, OCH2), 5.02
(d, J ¼ 15.20 Hz, 1H, OCH2), 6.76–7.53 (m, 6H, ArH), 8.38
(d, J ¼ 8.51 Hz, 1H, ArH); m/z ¼ 404, 402 (Mþ); Anal. calcd for
C20H15ClO3S2: C, 59.70; H, 3.73; Found C, 59.62; H, 3.58%.
Compound 5d. Yield (65%); white solid; m.p. 1208C; lmax (nm) 220
(log 1 ¼ 3.59), 270 (log 1 ¼ 3.75), 340 (log 1 ¼ 3.84); n
(cm21) 1710,
¯
max
1580, 1560, 1220; dH (300 MHz) 2.17 (s, 3H, CH3), 2.27 (s, 3H, CH3), 3.62
(dd, J ¼ 9.10, 11.22 Hz, 1H, SCH2), 3.69 (dd, J ¼ 7.20, 11.22 Hz, 1H,
SCH2), 5.01 (dd, J ¼ 7.20, 9.10 Hz, 1H, CH), 4.85 (d, J ¼ 15.20 Hz, 1H,
OCH2), 5.00 (d, J ¼ 15.20 Hz, 1H, OCH2), 6.63–7.53 (m, 6H, ArH), 8.38
(d, J ¼ 8.51 Hz, 1H, ArH); m/z ¼ 418, 416 (Mþ); Anal. calcd for
C21H17ClO3S2: C, 60.58; H, 4.09; Found C, 60.49; H, 4.25%.
Compound 5e. Yield (68%); white solid; m.p. 1618C; lmax (nm) 220
(log 1 ¼ 3.51), 272 (log 1 ¼ 3.67), 336 (log 1 ¼ 3.81); n
(cm21) 1710,
¯
max
1600, 1570, 1280; dH (300 MHz) 2.17 (s, 3H, CH3), 2.23 (s, 3H, CH3), 3.60
(dd, J ¼ 9.10, 11.22 Hz, 1H, SCH2), 3.67 (dd, J ¼ 7.20, 11.22 Hz,
1H, SCH2), 4.99 (dd, J ¼ 7.20, 9.10 Hz, 1H, CH), 4.88 (d, J ¼ 15.20 Hz,
1H, OCH2), 5.06 (d, J ¼ 15.20 Hz, 1H, OCH2), 6.55–7.52 (m, 6H, ArH),
8.38 (d, J ¼ 8.51 Hz, 1H, ArH); m/z ¼ 418, 416 (Mþ); Anal. calcd for
C21H17ClO3S2: C, 60.58; H, 4.09; Found C, 60.43; H, 4.23%.
Compound 5f. Yield (70%); white solid; m.p. 1308C; lmax (nm) 233
(log 1 ¼ 4.33), 267 (log 1 ¼ 4.34), 342 (log 1 ¼ 4.06); n
(cm21) 1720,
¯
max
1590, 1570, 1210; dH (300 MHz) 3.61 (dd, J ¼ 9.10, 11.22 Hz, 1H, SCH2),
3.69 (dd, J ¼ 7.20, 11.22 Hz, 1H, SCH2), 3.73 (s, 3H OCH3), 5.01 (dd,
J ¼ 7.20, 9.10 Hz, 1H, CH), 4.88 (d, J ¼ 15.20 Hz, 1H, OCH2), 4.95
(d, J ¼ 15.20 Hz, 1H, OCH2), 6.80–7.58 (m, 7H, ArH), 8.47
(d, J ¼ 8.51 Hz, 1H, ArH); m/z ¼ 420, 418 (Mþ); Anal. calcd for
C21H17ClO3S2: C, 57.42; H, 3.83; Found C, 57.83; H, 3.91%.
ACKNOWLEDGMENTS
We are thankful to CSIR (New Delhi) for financial assistance. One of us
(SKG) is grateful to CSIR (New Delhi) for a fellowship.