127.33 (t), 128.76 (t), 129.15 (t), 131.29 (q), 132.84 (q), 139.30
(q); MS (EI) Mϩ 263. Anal. Calcd for C13H13NO3S: C, 59.30; H,
4.98; N, 5.32. Found: C, 59.35; H, 4.89; N, 5.29%.
Hara for the measurements of HRMS and Dr. Hiroko Seki and
Ms. Yukiko Hiramoto for elemental analysis in the Chemical
Analysis Center of Chiba University.
N-Methoxy-1,3-dihydrobenzisothiazole 2,2-dioxide (7)
References
Oil; IR (neat) 3000, 2940, 2820, 1590, 1500, 1360, 1160 cmϪ1; 1H
NMR (400 MHz, CDCl3) δ 4.14 (s, 3H), 4.34 (s, 2H), 7.22 (m,
2H), 7.39 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 49.97 (s),
65.88 (p), 120.02 (q), 125.67 (t), 126.23 (t), 128.81 (t), 129.79 (t),
142.39 (q); HRMS (FAB) Found Mϩ 199.0288. Calcd for
C8H9NO3S M 199.0303.
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N-Methoxy-1,3,4,5-tetrahydro-2,1-benzothiazepine 2,2-dioxide
(9)
Mp 127.0–129.0 ЊC; IR (KBr) 2980, 2860, 2825, 1600,
1
1490, 1360, 1160 cmϪ1; H NMR (400 MHz, CDCl3) δ 2.16 (t,
J = 5.8 Hz, 2H), 3.04 (t, J = 5.1 Hz, 2H), 3.71 (t, J = 6.1 Hz, 2H),
3.89 (s, 3H) 7.17 (td, J = 7.9, 1.5 Hz, 1H), 7.24–7.34 (m, 2H),
7.43 (dd, J = 3.8, 1.7 Hz, 1H); 13C NMR (100 MHz, CDCl3)
δ 24.96 (s), 32.84 (s), 51.40 (s), 64.37 (p), 127.88 (t), 130.86 (t),
131.77 (t), 132.39 (t), 138.45 (q), 141.73 (q); MS (EI) Mϩ 227.
Anal. Calcd for C10H13NO3S: C, 52.85; H, 5.77; N, 6.16. Found:
C, 52.52; H, 5.54; N, 6.14%.
1-Methoxy-9-benzenesulfonyl-3,4-dihydro-2,1-indolothiazine
2,2-dioxide (11)
Mp 162.0 ЊC (decomp.); IR (KBr) 3100, 2990, 2950, 2820, 1600,
1
1480, 1360, 1160 cmϪ1; H NMR (400 MHz, CDCl3) δ 2.51
(ddd, J = 13.3, 9.9, 8.4 Hz, 1H), 2.78 (s, 3H), 2.98 (ddd, J = 13.4,
8.9, 3.0 Hz, 1H), 3.37–3.48 (m, 2H), 6.21 (s, 1H), 7.13 (td,
J = 7.5, 1.0 Hz, 1H), 7.32 (dd, J = 7.6, 0.8 Hz, 1H), 7.39–7.49
(m, 2H), 7.56 (tt, J = 7.4, 1.3 Hz, 1H), 7.66 (d, J = 8.2 Hz, 1H),
7.89 (dt, J = 7.3, 1.3 Hz, 1H); 13C NMR (100 MHz, CDCl3)
δ 24.44 (s), 46.48 (s), 64.91 (p), 73.30 (q), 85.41 (q), 114.42 (t),
124.43 (t), 125.62 (t), 127.47 (t), 128.11 (q), 129.06 (t), 131.40
(t), 133.48 (t), 137.60 (q), 141.03 (q); MS (FAB) Mϩ ϩ 1 393.
Anal. Calcd for C17H16N2O5S2: C, 52.03; H, 4.11; N, 7.14.
Found: C, 51.91; H, 4.02; N, 7.05%.
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3,4-Dihydro-2,1-benzothiazine 2,2-dioxide
1
Mp 150.0–152.0 ЊC (lit.5d 151–153 ЊC); H NMR (400 MHz,
CDCl3) δ 3.32 (t, J = 6.9 Hz, 2H), 3.49 (t, J = 6.8, 2H), 6.45 (s,
1H), 6.75 (dd, J = 8.1, 1.1 Hz, 1H), 7.05 (td, J = 7.5, 1.1 Hz, 1H),
7.17–7.23 (m, 2H)
Acknowledgement
Financial support from a Grant-in-Aid for Scientific Research
(No.13554028) from the Ministry of Education, Science, Sports
and Culture is gratefully acknowledged. We thank Ms. Ritsuko
10 A. A. Rudolpr and D. H. William, J. Am. Chem. Soc., 1981, 103,
1525.
O r g . B i o m o l . C h e m . , 2 0 0 3 , 1, 1 3 4 2 – 1 3 4 6
1346