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3-Bromo-6-(2-methoxyphenyl)-11H-benzo[5,6][1,4]thiazino[3,4-
3-Chloro-6-(2-uorophenyl)-11H-benzo[5,6][1,4]thiazino[3,4-a]
a]isoindol-11-one (5h). Yield: 87% as a yellow solid, mp 160– isoindol-11-one (5l). Yield: 87% as a yellow solid, mp 274–280 ꢀC;
165 ꢀC; FTIR (KBr): nmax ¼ 3066 (s), 2987 (s), 1689 (s), 1646 (m), FTIR (KBr): nmax ¼ 3062 (s), 1689 (s), 1646 (m), 1568 (m), 1483
1575 (m), 1482 (s) cmꢁ1; 1H NMR (400 MHz, CDCl3): d 9.09 (d, J (s) cmꢁ1; 1H NMR (400 MHz, CDCl3): d 9.13 (d, J ¼ 9.04 Hz, 1H,
¼ 9.04 Hz, 1H, H-1), 7.93 (d, J ¼ 7.76 Hz, 1H, H-10), 7.51–7.55 H-1), 7.95 (d, J ¼ 7.64 Hz, 1H, H-10), 7.54–7.59 (m, 1H, H-9),
(m, 1H, H-9), 7.41–7.45 (m, 1H, H-8), 7.26–7.37 (m, 4H, H-30, H- 7.45–7.49 (m, 2H, H-8, H-30), 7.19–7.36 (m, 4H, H-2, H-40, H-50,
40, H-50, H-60), 7.07–7.13 (m, 2H, H-2, H-4), 6.47 (d, J ¼ 8.00 Hz, H-60), 7.07 (d, J ¼ 2.36 Hz, 1H, H-4), 6.49 (d, J ¼ 8.00 Hz, 1H, H-
1H, H-7), 3.79 (s, 3H, OCH3) ppm; 13C NMR (400 MHz, CDCl3): 7) ppm; 13C NMR (100 MHz, CDCl3): d 165.13 (C-11), 160.17 (d,
d 165.19 (C-11), 157.56 (C-20), 133.07, 131.86, 131.73, 131.38, JC–F ¼ 249.44 Hz), 132.43, 132.25 (d, JC–F ¼ 7.96 Hz), 132.11,
131.04, 130.23, 128.40, 128.10, 127.77, 127.50, 124.45, 123.03, 131.78 (d, JC–F ¼ 1.73 Hz), 130.70, 130.60, 128.90, 128.43, 128.25,
122.73, 121.66, 121.60, 120.61, 117.86, 114.15, 111.94, 55.90 127.61, 125.46 (d, JC–F ¼ 3.77 Hz), 125.03, 123.29, 121.72 (d, JC–F
(OCH3) ppm; HRMS (ESI+) m/z calcd for C22H14BrNO2S [M + H]+ ¼ 13.55 Hz), 121.35, 120.39, 118.17, 116.90 (d, JC–F ¼ 21.44 Hz),
434.9929, found 434.9899.
6-(2-Fluorophenyl)-11H-benzo[5,6][1,4]thiazino[3,4-a]isoindol-
11-one (5i). Yield: 75% as a yellow solid, mp 220–224 C; FTIR
110.30 ppm; HRMS (ESI+) m/z calcd for C21H11ClFNOS [M + H]+
380.0312, found 380.0305.
ꢀ
3-Bromo-6-(2-uorophenyl)-11H-benzo[5,6][1,4]thiazino[3,4-a]
(KBr): nmax ¼ 3061 (s), 1687 (s), 1649 (m), 1608 (m), 1573 (m), isoindol-11-one (5m). Yield: 83% as a yellow solid, mp 254–
1523 (w), 1479 (m) cmꢁ1; 1H NMR (400 MHz, CDCl3): d 9.06 (d, J 260 ꢀC; FTIR (KBr): nmax ¼ 3061 (s), 1701 (s), 1660 (m), 1566 (m),
¼ 9.04 Hz, 1H, H-1), 7.96 (d, J ¼ 7.64 Hz, 1H, H-10), 7.44–7.50 1487 (m), 1473 (m), 1456 (m) cmꢁ1; 1H NMR (400 MHz, CDCl3):
(m, 2H, H-8, H-9), 7.24–7.36 (m, 3H, H-40, H-50, H-60), 7.07–7.10 d 9.07 (d, J ¼ 9.08 Hz, 1H, H-1), 7.96 (d, J ¼ 7.68 Hz, 1H, H-10),
(m, 4H, H-2, H-4, H-3, H-20), 6.49 (d, J ¼ 8.00 Hz, 1H, H-7) ppm; 7.55–7.60 (m, 1H, H-9), 7.45–7.49 (m, 2H, H-8, H-30), 7.28–7.37
13C NMR (100 MHz, CDCl3): d 165.21 (C-11), 160.16 (d, JC–F
¼
(m, 4H, H-2, H-40, H-50, H-60), 7.22 (d, J ¼ 2.32 Hz, 1H, H-4), 6.50
250.24 Hz), 133.81, 132.91, 132.26 (d, JC–F ¼ 8.07 Hz), 131.89, (d, J ¼ 8.64 Hz, 1H, H-7) ppm; 13C NMR (100 MHz, CDCl3):
131.81 (d, JC–F ¼ 1.83 Hz), 131.77, 130.71, 130.55, 128.90, 128.63, d 165.15 (C-11), 160.16 (d, JC–F ¼ 249.55 Hz), 132.93, 132.25 (d,
127.82, 125.47 (d, JC–F ¼ 1.83 Hz), 123.20, 122.12 (d, JC–F ¼ 16.06 JC–F ¼ 8.01 Hz), 132.13, 131.77 (d, JC–F ¼ 1.83 Hz), 130.71,
Hz), 121.26, 120.65, 119.52 (d, JC–F ¼ 17.44 Hz), 118.09, 130.57, 128.90, 128.41, 128.26, 127.82, 125.47 (d, JC-F ¼ 3.71 Hz),
116.94 ppm; HRMS (ESI+) m/z calcd for C21H12FNOS [M + H]+ 123.30, 121.97, 121.70 (d, JC–F ¼ 15.93 Hz), 121.35, 120.66,
346.0702, found 346.0717.
6-(2-Fluorophenyl)-3-methyl-11H-benzo[5,6][1,4]thiazino[3,4-a]
isoindol-11-one (5j). Yield: 85% as a yellow solid, mp 240–244 ꢀC;
118.10, 116.91 (d, JC–F ¼ 21.08 Hz), 110.37 ppm; HRMS (ESI+) m/
z calcd for C21H11BrFNOS [M + H]+ 423.9807, found 423.9814.
6-(3-Fluorophenyl)-11H-benzo[5,6][1,4]thiazino[3,4-a]isoindol-
ꢀ
FTIR (KBr): nmax ¼ 3059 (s), 1683 (s), 1649 (m), 1608 (m), 1576 11-one (5n). Yield: 78% as a yellow solid, mp 185–190 C; FTIR
1
(m), 1489 (s) cmꢁ1; H NMR (400 MHz, CDCl3): d 9.06 (d, J ¼ (KBr): nmax ¼ 3062 (s), 1693 (s), 1643 (m), 1606 (m), 1585 (m),
8.60 Hz, 1H, H-1), 7.95 (d, J ¼ 7.64 Hz, 1H, H-10), 7.43–7.58 (m, 1481 (s) cmꢁ1; 1H NMR (400 MHz, CDCl3): d 9.17 (d, J ¼ 8.80 Hz,
4H, H-8, H-9, H-30, H-40), 7.25–7.36 (m, 4H, H-2, H-4, H-50, H-60), 1H, H-1), 7.96 (d, J ¼ 7.72 Hz, 1H, H-10), 7.44–7.56 (m, 2H, H-8,
6.48 (d, J ¼ 7.96 Hz, 1H, H-7), 2.30 (s, 3H, CH3) ppm; 13C NMR H-9), 7.23–7.31 (m, 3H, H-40, H-50, H-60), 6.99–7.11 (m, 4H, H-2,
(100 MHz, CDCl3): d 165.04 (C-11), 160.20 (d, JC–F ¼ 249.35 Hz), H-3, H-4, H-20), 6.55 (d, J ¼ 7.96 Hz, 1H, H-7) ppm; 13C NMR (100
135.46, 131.99 (d, JC–F ¼ 7.91 Hz), 131.87 (d, JC–F ¼ 1.76 Hz), MHz, CDCl3): d 165.23 (C-11), 163.30 (d, JC–F ¼ 247.69 Hz),
131.71, 131.34, 130.71, 128.89, 128.56, 128.43, 127.61, 125.84, 136.64 (d, JC–F ¼ 8.18 Hz), 133.80, 132.03, 131.95, 131.70, 131.45
125.35 (d, JC–F ¼ 3.82 Hz), 125.03, 123.10, 121.29 (d, JC–F ¼ 11.62 (d, JC–F ¼ 8.41 Hz), 128.92 (d, JC–F ¼ 8.07 Hz), 128.43, 127.89,
Hz), 120.39, 119.28, 116.81 (d, JC–F ¼ 21.27 Hz), 111.11, 20.64 125.42 (d, JC–F ¼ 3.07 Hz), 123.22, 121.78, 119.44, 117.89, 117.65,
(CH3) ppm; HRMS (ESI+) m/z calcd for C22H14FNOS [M + H]+ 117.14, 116.80 (d, JC–F ¼ 21.92 Hz), 116.00, 115.79 ppm; HRMS
360.0858, found 360.0841.
6-(2-Fluorophenyl)-3-methoxy-11H-benzo[5,6][1,4]thiazino[3,4-
a]isoindol-11-one (5k). Yield: 76% as a yellow solid, mp 266–
(ESI+) m/z calcd for C21H12FNOS [M + H]+ 346.0702, found
346.0673.
6-(3-Fluorophenyl)-3-methyl-11H-benzo[5,6][1,4]thiazino[3,4-a]
270 ꢀC; FTIR (KBr): nmax ¼ 3060 (s), 1690 (s), 1649 (m), 1604 (m), isoindol-11-one (5o). Yield: 85% as a yellow solid, mp 220–
1568 (m), 1496 (s) cmꢁ1; 1H NMR (400 MHz, CDCl3): d 9.14 (d, J 224 ꢀC; FTIR (KBr): nmax ¼ 3062 (s), 1681 (s), 1645 (m), 1606 (m),
¼ 9.32 Hz, 1H, H-1), 7.94 (d, J ¼ 7.64 Hz, 1H, H-10), 7.53–7.59 1583 (m), 1490 (s) cmꢁ1; 1H NMR (400 MHz, CDCl3) d ¼ 9.04 (d, J
(m, 1H, H-9), 7.43–7.50 (m, 2H, H-8, H-30), 7.25–7.35 (m, 3H, H- ¼ 8.60 Hz, 1H, H-1), 7.93 (d, J ¼ 7.64 Hz, 1H, H-10), 7.42–7.54
40, H-50, H-60), 6.80 (dd, J ¼ 9.28 and 2.92 Hz, 1H, H-4), 6.64 (d, J (m, 2H, H-8, H-9), 7.21–7.31 (m, 4H, H-20, H-40, H-50, H-60), 7.06
¼ 2.88 Hz, 1H, H-2), 6.48 (d, J ¼ 8.60 Hz, 1H, H-7), 3.81 (s, 3H, (dd, J ¼ 8.60 and 1.48 Hz, 1H, H-2), 6.90 (d, J ¼ 1.56 Hz, 1H, H-4),
OCH3) ppm; 13C NMR (100 MHz, CDCl3): d 164.84 (C-11), 160.23, 6.52 (d, J ¼ 8.0 Hz, 1H, H-7) ppm; 13C NMR (100 MHz, CDCl3)
156.70, 132.04 (d, JC–F ¼ 7.98 Hz), 131.91 (d, JC–F ¼ 1.79 Hz), d ¼ 165.03 (C-11), 163.27 (d, JC–F ¼ 247.57 Hz), 136.74 (d, JC–F
¼
131.63, 130.65, 128.62, 128.58, 128.49, 127.20, 125.36 (d, JC–F
¼
8.05 Hz), 135.45, 131.51, 131.39 (d, JC–F ¼ 8.40 Hz), 131.29,
3.76 Hz), 123.03, 122.11 (d, JC–F ¼ 15.91 Hz), 121.23, 120.88, 130.54, 128.50 (d, JC–F ¼ 2.92 Hz), 127.15, 125.77, 125.44 (d, JC–F
120.64, 116.82 (d, JC–F ¼ 21.19 Hz), 112.63, 110.86, 110.37, 55.55 ¼ 3.03 Hz), 123.10, 121.74, 119.28, 117.06, 116.93, 116.78 (d, JC–F
(OCH3) ppm; HRMS (ESI+) m/z calcd for C22H14FNO2S [M + H]+ ¼ 14.11 Hz), 116.60, 116.58, 20.66 ppm; HRMS (ESI+) m/z calcd
376.0808, found [M + H]+ 376.0802.
for C22H14FNOS [M + H]+ 360.0858, found 360.0890.
12790 | RSC Adv., 2019, 9, 12784–12792
This journal is © The Royal Society of Chemistry 2019