ABAEE and CHERAGHI/Turk J Chem
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06 (M+-CO2 Et), 29 (Et). Anal. Calcd. for C10 H13 NO2 (Mw 179.22): C, 67.02; H, 7.31; N, 7.82. Found: C,
7.21; H, 7.09; N, 7.55%.
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-Amino-5,7-dihydro-4H -thieno[2,3-c]thiopyran-3-carbonitrile (4aa). Light brown solid, mp 205–207 C;
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H NMR (500 MHz, DMSO-d6) δ 2.58–2.61 (m, 2H), 2.84–2.86 (m, 2H), 3.53 (s, 2H), 7.05 (s, 2H) ppm; 13
C
NMR (125 MHz, DMSO-d6) δ 24.5, 25.4, 26.9, 84.6, 114.0, 116.7, 131.8, 163.0 ppm; IR (KBr) ν 3317, 3207,
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885, 2196, 1622, 1519 cm ; MS m/z (%) 196 (M ), 168 (M -CH2 CH2), 150 (M -CH2 S), 46 (CH2 S), 27
HCN). Anal. Calcd. for C8 H8 N2 S2 (Mw 196.29): C, 48.95; H, 4.11; N, 14.27. Found: C, 49.09; H, 4.28; N,
(
14.33%.
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Ethyl 2-amino-5,7-dihydro-4H-thieno[2,3-c]thiopyran-3-carboxylate (4ab). Orange solid, mp 86–89 C;
H NMR (500 MHz, CDCl3) δ 1.36 (t, J = 7.0 Hz, 3H), 2.88–2.90 (m, 2H), 3.03–3.05 (m, 2H), 3.59 (s, 2H),
.27–4.21 (q, J = 7.0 Hz, 2H), 6.05 (s, 2H) ppm; 13 C NMR (125 MHz, CDCl3) δ 14.9, 25.4, 26.6, 29.1, 60.0,
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06.5, 114.0, 132.7, 161.6, 166.2 ppm; IR (KBr) ν 3412, 3304, 2978, 2943, 2895, 1651, 1568, 1483 cm ; MS
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m/z (%) 243 (M ), 197 (M -CH2 S), 170 (M -CO2 Et), 46 (CH2 S), 29 (Et), 27 (HCN). Anal. Calcd. for
C10 H13 NO2 S2 (Mw 243.35): C, 49.36; H, 5.38; N, 5.76. Found: C, 49.48; H, 5.44; N, 5.89%.
-Amino-5,7-dihydro-4H -thieno[2,3-c]pyran-3-carbonitrile (4ba). Yellow solid, mp 215–218 C; 1
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H
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NMR (500 MHz, DMSO-d6) δ 2.82–2.84 (m, 2H), 3.91–3.93 (m, 2H), 4.56 (s, 2H), 6.11 (br s, 2H) ppm;
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C NMR (125 MHz, DMSO-d6) δ 24.5, 63.8, 64.0, 84.1, 114.0, 115.7, 130.8, 163.3 ppm; IR (KBr) ν 3411,
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201, 1620, 1525 cm ; MS m/z (%) 180 (M ), 152 (M -CH2 CH2), 150 (M -CH2 O), 27 (HCN). Anal.
Calcd. for C8 H8 N2 OS (Mw 180.23): C, 53.31; H, 4.47; N, 15.54. Found: C, 53.52; H, 4.31; N, 15.66%.
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Ethyl 2-amino-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate (4bb). Yellow solid, mp 117–118 C; H
NMR (500 MHz, CDCl3) δ 1.34 (t, J = 7.0 Hz, 3H), 2.82–2.85 (m, 2H), 3.90–3.92 (m, 2H), 4.25 (q, J = 7.0
Hz, 2H), 4.56 (s, 2H), 6.11 (s, 2H) ppm; 13 C NMR (125 MHz, CDCl3) δ 14.9, 28.1, 60.0, 65.0, 65.5, 105.6,
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115.1, 130.7, 162.7, 166.2 ppm; IR (KBr) ν 3433, 3325, 2945, 2902, 2846, 1654, 1587, 1265, 1083, 1018 cm
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MS m/z (%) 227 (M ), 198 (M -Et), 73 (CO2 Et), 29 (Et). Anal. Calcd. for C10 H13 NO3 S (Mw 227.28): C,
2.85; H, 5.77; N, 6.18. Found: C, 52.58; H, 5.61; N, 6.00%.
-Amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile (4ca). White solid, mp 147–148 C; 1
NMR (500 MHz, CDCl3) δ 1.78–1.83 (m, 4H), 2.49–2.52 (m, 4H), 4.7 (s, 2H) ppm; 13 C NMR (125 MHz,
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H
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CDCl3) δ 22.5, 23.8, 24.5, 24.9, 88.8, 116.0, 120.9, 132.7, 160.6 ppm; IR (KBr) ν 3450, 3325, 2200 cm ; MS
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m/z (%) 178 (M ), 177 (M -1), 150 (M -CH2 CH2). Anal. Calcd. for C9 H10 N2 S (Mw 178.25): C, 60.64;
H, 5.65; N, 15.72. Found: C, 60.43; H, 5.79; N, 15.48%.
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Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (4cb). White solid, mp 114–115 C;
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H NMR (500 MHz, CDCl3) δ 1.34 (t, J = 7.0 Hz, 3H), 1.75–1.77 (m, 4H), 2.45–2.48 (m, 2H), 2.70–2.72 (m,
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H), 4.24 (q, J = 7.0 Hz, 2H), 6.00 (s, 2H) ppm; 13 C NMR (125 MHz, CDCl3) δ 14.9, 23.3, 23.7, 25.0, 27.4,
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9.8, 106.2, 118.1, 132.9, 162.1, 166.5 ppm; IR (KBr) 3405, 3300, 1650, cm ; MS m/z (%) 225 (M ), 196
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M -Et), 179 (M -HCOOH), 29 (Et). Anal. Calcd. for C11 H15 NO2 S (Mw 225.31): C, 58.64; H, 6.71; N,
.22. Found: C, 58.66; H, 6.77; N, 6.45%.
-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (4da). White solid, mp 147–148 C; 1
NMR (80 MHz, CDCl3) δ 2.3–2.4 (m, 2H), 2.7–2.8 (m, 2H), 2.8–2.9 (m, 2H), 5.9 (s, 2H) ppm; IR (KBr) ν
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H
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3
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440, 3335, 2190 cm ; MS m/z (%) 164 (M ), 148 (M -NH2), 28 (CN). Anal. Calcd. for C8 H8 N2 S (Mw
64.23): C, 58.51; H, 4.91; N, 17.06. Found: C, 58.66; H, 4.80; N, 16.89%.
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