ꢀ
ꢀ
M. Drabikova et al. / Tetrahedron 73 (2017) 6296e6306
6303
4.16. 2,2-di(prop-2-yn-1-yl)-2H-benzo[b][1,4]thiazin-3(4H)-one
1,1-dioxide 10d
4.19. 2-Cyclopentyl-2H-benzo[b][1,4]thiazin-3(4H)-one 1,1-dioxide
11b
Bright yellow solid (17 mg, 60% yield). 1H NMR (500 MHz,
DMSO-d6):
White solid (8 mg, 28% yield). 1H NMR (500 MHz, DMSO-d6):
d
11.19 (brs, 1H), 7.81 (dd, J ¼ 7.8, 1.4 Hz, 1H), 7.70e7.66
d
11.51 (brs, 1H), 7.81 (dd, J ¼ 7.9, 1.3 Hz, 1H), 7.75e7.71 (m, 1H),
(m, 1H), 7.32e7.29 (m, 1H), 7.21e7.19 (d, J ¼ 8.2, 0.7 Hz, 1H), 4.43 (d,
7.36e7.33 (m, 1H), 7.21 (dd, J ¼ 7.4, 0.8 Hz, 1H), 3.08 (t, J ¼ 2.7 Hz,
2H), 3.05 (d, J ¼ 2.5 Hz, 3H) ppm. 13C NMR (101 MHz, DMSO-d6):
J ¼ 9.0 Hz, 1H), 2.17e2.08 (m, 1H), 2.05e1.71 (m, 2H), 1.61e1.57 (m,
3H), 1.47e1.36 (m, 3H) ppm. 13C NMR (101 MHz, DMSO-d6):
d 164.4,
d
164.0, 135.8, 134.8, 124.5, 124.4, 122.2, 118.2, 76.5, 75.6, 65.5,
135.8, 135.1, 124.2, 123.8, 123.7, 118.2, 68.4, 36.6, 30.4, 23.8 ppm. IR
18.9 ppm. IR (nmax
e
) ¼ 3355 (w), 3271 (m), 3204e3083 (w), 2920
(
nmax
e
) ¼ 3353 (w), 3228 (w), 3154 (w), 2921 (w), 2852 (w), 1673 (s),
(m), 2850 (w),1676 (s), 1596 (m),1482 (m),1425 (m),1358 (m),1315
(s), 1297 (s), 1168 (s), 1153 (s), 1133 (s), 993 (m), 927 (m), 804 (m),
1595 (m), 1479 (m), 1357 (m), 1318 (s), 1205 (m), 1169 (m), 1114 (m),
760 (s) cmꢂ1
.
HRMS (ESI): m/z calcd for C13H15NO3S
757 (s) cmꢂ1
.
HRMS (ESI): m/z calcd for C14H11NO3S
[M ꢂ H]- ¼ 264.0700, found [M ꢂ H]- ¼ 264.0702.
[M ꢂ H]- ¼ 272.0387, found [M ꢂ H]- ¼ 272.0390.
4.17. Spiro[benzo[b][1,4]thiazine-2,10-cyclopentan]-3(4H)-one 1,1-
4.20. 2-Ethyl-6-methyl-2H-benzo[b][1,4]thiazin-3(4H)-one 1,1-
dioxide 11ba
dioxide 10e
Bright yellow solid (7 mg, 30% yield). 1H NMR (500 MHz, DMSO-
Bright yellow solid (21 mg, 79% yield). 1H NMR (500 MHz,
d6):
d
11.14 (brs, 1H), 7.69 (d, J ¼ 8.0 Hz, 1H), 7.13e7.11 (m, 1H), 6.99
DMSO-d6):
d
11.21 (brs, 1H), 7.83 (dd, J ¼ 7.8, 1.5 Hz, 1H), 7.72e7.68
(s, 1H), 4.46 (dd, J ¼ 7.8, 5.4 Hz, 1H), 2.37 (s, 3H), 2.01e1.94 (m, 1H),
1.90e1.83 (m, 1H), 1.08 (t, J ¼ 7.5 Hz, 3H) ppm. 13C NMR (126 MHz,
(m, 1H), 7.33e7.30 (m, 1H), 7.22 (dd, J ¼ 7.4, 0.8 Hz, 1H), 2.16e2.11
(m, 4H), 1.76e1.70 (m, 4H) ppm. 13C NMR (101 MHz, DMSO-d6):
DMSO-d6): d 164.6, 145.6, 135.7, 124.3, 123.5, 122.1, 118.2, 64.9, 21.2,
d
168.0, 135.5, 135.3, 124.3, 123.8, 123.4, 118.2, 71.2, 29.9, 26.2 ppm.
16.5, 11.7 ppm. IR (nmax
e
) ¼ 3050 (w), 3013 (w), 2972 (w), 2937 (w),
IR (nmax
e
) ¼ 3207 (w), 3064 (w), 2923 (w), 2852 (w), 1676 (s), 1595
1681 (s), 1604 (m), 1586 (m), 1470 (m), 1382 (m), 1334 (s), 1290 (m),
1214 (m), 1126 (s), 822 (s), 759 (m) cmꢂ1. HRMS (ESI): m/z calcd for
(m), 1482 (m), 1425 (m), 1350 (m), 1315 (s), 1297 (s), 1168 (s), 1123
(s), 1027e840 (m), 733 (s) cmꢂ1. HRMS (ESI): m/z calcd for
C
11H13NO3S [M ꢂ H]- ¼ 238.0543, found [M ꢂ H]- ¼ 238.0536.
C
12H13NO3S [M ꢂ H]- ¼ 250.0543, found [M ꢂ H]- ¼ 250.0550.
4.21. 2-Isopropyl-2H-benzo[b][1,4]thiazin-3(4H)-one 1,1-dioxide
11c
4.18. 2-Ethyl-2H-benzo[b][1,4]thiazin-3(4H)-one 1,1-dioxide 11a
Bright yellow solid (9 mg, 37% yield). 1H NMR (500 MHz, DMSO-
Bright yellow solid (11 mg, 43% yield). 1H NMR (500 MHz,
d6):
d
10.88 (brs, 1H), 7.81 (dd, J ¼ 7.8, 1.4 Hz, 1H), 7.70e7.66 (m, 1H),
DMSO-d6):
d
11.22 (brs, 1H), 7.80 (dd, J ¼ 7.8, 1.4 Hz, 1H), 7.69e7.66
7.32e7.29 (m, 1H), 7.21 (dd, J ¼ 8.1, 0.8 Hz, 1H), 4.53 (dd, J ¼ 7.7,
(m, 1H), 7.32e7.28 (m, 1H), 7.20 (dd, J ¼ 8.2, 0.8 Hz, 1H), 4.38 (d,
5.4 Hz, 1H), 2.00e1.86 (m, 2H), 1.09 (appt, J ¼ 7.5 Hz, 3H) ppm. 13
C
J ¼ 5.3 Hz, 1H), 2.38e2.30 (m, 1H), 1.16 (d, J ¼ 6.9 Hz, 3H), 0.97 (d,
NMR (126 MHz, DMSO-d6):
d
164.9, 136.3, 135.6, 125.3, 124.1, 124.1,
J ¼ 6.9 Hz, 3H) ppm. 13C NMR (101 MHz, DMSO-d6):
d 164.0, 135.9,
118.8, 65.3, 16.9, 12.3 ppm. IR (nmax
e
) ¼ 3188 (w), 3131 (w), 3056 (w),
135.1, 125.0, 123.7, 123.3, 118.2, 69.2, 26.6, 20.9, 19.2 ppm. IR
2978 (w), 2971 (w),1673 (s),1595 (m),1478 (m),1425 (m),1361 (m),
(
nmax
e
) ¼ 3352 (w), 3192e3054 (w), 2962 (w), 2919 (m), 2851 (w),
1314 (s), 1210 (m), 1168 (s), 1124 (s), 1026e821 (m), 725 (s) cmꢂ1
.
1681 (s), 1677 (m), 1594 (m), 1478 (m), 1392 (m), 1359 (m), 1252
HRMS (ESI): m/z calcd for C10H11NO3S [M ꢂ H]- ¼ 224.0387, found
(m),1224 (m),1126 (s),1072 (m), 869 (s), 760 (m) cmꢂ1. HRMS (ESI):
[M ꢂ H]- ¼ 224.0372.
m/z calcd for
C
11H13NO3S [M
ꢂ
H]-
¼
238.0543, found