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HETEROCYCLES, Vol. 83, No. 6, 2011
(M+) 293. Anal. Calcd for C19H19NS: C, 77.77; H, 6.53; N, 4.77. Found: C, 77.59; H, 6.53; N, 4.94.
X-Ray crystallographic data for 4c: Mr = 293.41, a = 11.512(8) Å, b = 12.053(8) Å, c = 24.029(16) Å,
V = 3218(4) Å3, T = 293 K, monoclinic, space group P21/a, Z = 8, 6342 dependent reflections, R1 =
0.0575, wR2 = 0.1278. Crystallographic data have been deposited with Cambridge Crystallographic
Data Centre. Deposition number CCDC-815982.
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(Z)-4-Benzylidene-2-methyl-4H-3,1-benzothiazine (4d): yellow oil, H NMR (CDCl3) = 2.36 (s, 3H,
CH3), 7.02 (s, 1H, =CH), 7.30-7.46 (m, 8H, Ar), 7.61 (d, 1H, J = 7.8 Hz, Ar). 13C NMR (CDCl3) =
27.90 (CH3), 121.51 (=CH), 124.39, 124.88, 126.56, 127.74, 128.52, 128.78, 128.91, 129.40, 129.96,
135.95, 142.40 (Ar), 158.91(C=N). HRMS: Calcd for C16H13NS; 251.0769. Found; 251.0776 (M+).
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(Z)-4-Benzylidene-2-(p-tolyl)-4H-3,1-benzothiazine (4f): yellow needles: mp146-148 C, H NMR
(CDCl3) = 2.41 (s, 3H, CH3), 7.12 (s, 1H, =CH), 7.24-7.26 (m, 2H, Ar), 7.31-7.39 (m, 2H, Ar),
7.43-7.47 (m, 3H, Ar), 7.53-7.57 (m, 3H, Ar), 7.64 (d, 1H, J= 8.0 Hz, Ar), 7.94 (d, 2H, J= 8.0 Hz, Ar).
13C NMR (CDCl3) = 21.83 (CH3), 122.52 (=CH), 124.53, 126.06, 126.29, 127.74, 128.56, 128.57,
128.58, 129.53, 129.56, 129.65, 129.91, 135.00, 136.08, 142.28, 143.23 (Ar), 158.01 (C=N). EI-MS:
Calcd for C22H17NS; 327. Found; (M+) 327. Anal. Calcd for C22H17NS: C, 80.47; H, 5.42; N, 4.21.
Found: C, 80.70; H, 5.23; N, 4.28.
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(Z)-4-Benzylidene-2-(p-methoxyphenyl)-4H-3,1-benzothiazine (4g): yellow needles: mp124-126 C, H
NMR (CDCl3) = 3.86 (s, 3H, OCH3), 6.94 (d, 2H, J = 6.8 Hz, Ar), 7.12 (s, 1H, =CH), 7.34-7.38 (m, 2H,
Ar), 7.43 (dd, 3H, J = 7.6 Hz and 8.0 Hz, Ar), 7.52 (dd, 3H, J = 7.6 Hz and 8.0 Hz, Ar), 7.63 (d, 1H, J =
7.6 Hz, Ar), 8.02 (d, 2H, J = 6.8 Hz, Ar).
13C NMR (CDCl3) = 55.68 (OCH3), 114.14 (Ar), 122.48
(=CH), 124.55, 126.05, 126.37, 127.74, 128.56, 128.35, 128.56, 129.39, 129.51, 129.68, 129.90, 130.32,
136.13, 143.36, 157.38 (Ar), 162.71 (C=N). EI-MS: Calcd for C22H17NOS; 343. Found; 343 (M+).
Anal. Calcd for C22H17NOS: C, 76.94; H, 4.99; N, 4.08. Found: C, 76.85; H, 5.05; N, 4.28.
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(Z)-4-Benzylidene-2-(p-chlorophenyl)-4H-3,1-benzothiazine (4h): yellow needles, mp 153-155 C, H
NMR (CDCl3) = 7.13 (s, 1H, =CH), 7.33-7.48 (m, 7H, Ar), 7.51-7.53 (m, 3H, Ar), 7.65 (d, 1H, J = 7.6
Hz, Ar), 7.99 (d, 2H, J = 8.4 Hz, Ar). 13C NMR (CDCl3) = 121.14 (=CH), 123.29, 124.34, 125.31,
126.61, 127.31, 127.38, 127.70, 127.73, 128.14, 128.31, 128.72, 134.57, 134.71, 136.60, 141.64 (Ar),
155.45 (C=N). EI-MS: Calcd for C21H14ClNS; 347. Found; 347 (M+). Anal. Calcd for C21H14ClNS: C,
72.51; H, 4.06; N, 4.03. Found: C, 72.53; H, 4.10; N, 4.23.
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(Z)-4-Benzylidene-2-(p-trifluoromethylphenyl)-4H-3,1-benzothiazine (4i): yellow oi1, H NMR (CDCl3)
= 7.14 (s, 1H, =CH), 7.34-7.57 (m, 8H, Ar), 7.66-7.71 (m, 3H, Ar), 8.16 (d, 2H, J = 8.4 Hz, Ar). 13C
NMR (CDCl3) = 122.38 (=CH), 124.55, 125.31 (Ar), 125.64 (q, J = 15.0 Hz, CF3), 126.74, 127.95,
127.97, 128.61, 129.37, 129.55, 129.85, 130.07, 132.96, 133.28, 135.77, 140.69, 142.74 (Ar), 156.49