PAPER
Regioselective Ring Opening of Aziridines
2385
4b
3f
Liquid.
Liquid.
1
IR (KBr): 3270, 2940, 2870, 2100, 1600 cm .
1H NMR (CDCl3): = 2.40 (s, 3 H), 3.50 (d, 2 H, J = 6.0 Hz), 4.45
(dd, 1 H, J = 12.8, 6.0 Hz), 5.20 (br s, 1 H, NH), 4.80–4.90 (br s,
NH), 7.10–7.40 (m, 7 H), 7.70 (d, 2 H, J = 8.0 Hz).
1H NMR (CDCl3): = 1.15–1.50 (m, 4 H), 1.60–1.80 (m, 2 H),
1.95–2.20 (m, 2 H), 2.45 (s, 3 H), 3.05 (ddd, 1 H, J = 10.0, 9.5, 4.0
Hz), 3.25 (ddd, 1 H, J = 9.5, 9.5, 3.8 Hz), 4.80 (br s, NH), 7.35 (d,
2 H, J = 8.0 Hz), 7.80 (d, 2 H, J = 8.0 Hz).
MS-EI: m/z = 295 [M+], 252, 210, 155, 111, 91.
HRMS: m/z calcd for C13 H18NO2S (M – N3)+, 252.10; found,
2g
Liquid.
1
IR (KBr): 3275, 2108, 1599 cm .
1H NMR (CDCl3): = 2.35 (s, 3 H), 2.43 (s, 3 H), 2.95–3.10 (m, 1
H), 3.15–3.20 (m, 1 H), 4.50 (dd, 1 H, J = 8.7, 5.2 Hz), 4.80–4.90
(br s, NH), 7.10–7.25 (m, 4 H), 7.30 (d, 2 H, J = 8.0 Hz), 7.80 (d, 2
H, J = 8.0 Hz).
252.10.
4c
Solid.
MS-EI: m/z = 330 [M+], 288 [M – N3]+, 275, 183, 155, 91.
Mp 147–148 °C.
Anal. Calcd for C16H18N4O2S (330.40): C, 58.16; H, 5.49; N, 16.96;
S, 9.70. Found: C, 58.20; H, 5.50; N, 17.01; S, 9.73
1
IR (KBr): 3270, 2935, 2870, 2098, 1598 cm .
1H NMR (CDCl3): = 1.20–1.40 (m, 6 H), 1.42–1.70 (m, 4 H),
1.80–1.90 (m, 1 H), 2.42 (s, 3 H), 3.05–3.10 (m, 1 H), 4.65 (br s,
NH), 7.33 (d, 2 H, J = 8.0 Hz), 7.80 (d, 2 H, J = 8.0 Hz).
3g
Liquid.
MS-EI: m/z = 307 [M+], 266, 210, 155, 125, 91.
1H NMR (CDCl3): = 2.39 (s, 3 H), 2.45 (s, 3 H), 3.5 (d, 1 H, J = 5.9
Hz), 3.15–3.20 (m, 1 H), 4.50 (dd, 1 H, J = 12.5, 5.9 Hz), 5.25 (br
s, NH), 7.10–7.29 (m, 4 H), 7.33 (d, 2 H, J = 8.0 Hz), 7.75 (d, 2 H,
J = 8.0 Hz).
Anal. Calcd for C14H20N4O2S (308.39): C, 54.53; H, 6.54; N, 18.17;
S, 10.40. Found: C, 54.40; H, 6.57; N, 18.37; S, 10.43.
4d
Solid.
2h
Solid.
Mp 107–109 °C.
MP 120–122 °C.
1
IR (KBr): 3253, 2935, 2243, 1600 cm .
1
IR (KBr): 3250, 2253, 1598 cm .
1H NMR (CDCl3): = 1.38–1.59 (m, 1 H), 1.60–1.78 (m, 3 H),
1.90–2.05 (m, 2 H), 2.45 (s, 3 H), 2.80–3.0 (m, 1 H), 3.68–3.88 (m,
1 H), 5.45 (br s, NH), 7.38 (d, 2 H, J = 8.1 Hz), 7.80 (d, 2 H, J = 8.1
Hz).
1H NMR (CDCl3): = 2.40 (s, 3 H), 2.80–3.0 (m, 2 H), 4.50–4.60
(m, 1 H), 5.45 (br s, NH), 7.10–7.48 (m, 7 H), 7.80 (d, 2 H, J = 8.0
Hz).
MS-EI: m/z = 301 [M+], 260, 155, 91.
MS-EI: m/z = 264 [M+], 237, 210, 155, 91.
Anal. Calcd for C16H16N2O2S (300.37): C, 64.0; H, 5.37; N, 9.33; S,
10.67. Found: C, 64.03; H, 5.36; N, 9.40; S, 10.7.
Anal. Calcd for C13H16N2O2S (264.34): C, 59.07; H, 6.10; N, 10.60;
S, 12.13. Found: C, 59.01; H, 6.07; N, 10.58; S, 12.15.
3i
4e
Liquid.
Solid.
1
IR (KBr): 3280, 2105, 1595 cm .
Mp 112–113 °C.
1H NMR (CDCl3): = 0.85 (t, 3 H, J = 7.0 Hz), 1.05–1.30 (m, 4 H),
1.35–1.50 (m, 2 H), 2.45 (s, 3 H), 3.25–3.35 (m, 3 H), 4.80 (d, 1 H,
J = 7.0 Hz), 7.38 (d, 2 H, J = 8.0 Hz), 7.80 (d, 2 H, J = 8.0 Hz).
1
IR (KBr): 3278, 2940, 2245, 1600 cm .
1H NMR (CDCl3): = 1.20–1.50 (m, 3 H), 1.51–1.80 (m, 3 H),
1.87–2.20 (m, 2 H), 2.45 (s, 3 H), 2.61–2.87 (m, 1 H), 3.32–3.52 (m,
1 H), 5.25 (br s, NH), 7.35 (d, 2 H, J = 8.0 Hz), 7.80 (d, 2 H, J = 8.0
Hz).
MS-EI: m/z = 296 [M+], 240 [M – CH2N3]+, 155, 91.
Anal. Calcd for C14H20N4O2S (296.38): C, 52.68; H, 6.80; N, 18.90;
S, 10.82. Found: C, 52.70; H, 6.78; N, 18.87; S, 10.85.
MS-EI: m/z = 278 [M+], 210, 155, 111, 91.
Anal. Calcd for C14H18N2O2S (278.36): C, 60.41; H, 6.52; N, 10.06;
S, 11.52. Found: C, 60.56; H, 6.50; N, 10.10; S, 11.55.
2i
1H NMR (CDCl3): = 0.90 (t, 3 H, J = 7.0 Hz), 1.25–1.38 (m, 4 H),
1.47–1.55 (m, 2 H), 2.45 (s, 3 H), 2.75–2.82 (m, 1 H), 3.05–3.15 (m,
1 H), 3.38–3.45 (m, 1 H), 4.85 (br s, 1 H, NH), 7.35 (d, 2 H, J = 8.0
Hz), 7.70 (d, 2 H, J = 8.0 Hz).
2f
Liquid.
1
IR (KBr): 3280, 2110, 1600 cm .
3j
Liquid.
1H NMR (CDCl3): = 2.40 (s, 3 H), 3.05–3.10 (m, 1 H), 3.15–3.30
(m, 1 H), 4.50–4.60 (dd, 1 H, J = 8.7, 5.2 Hz), 4.80–4.90 (br s, NH),
7.10–7.35 (m, 7H), 7.80 (d, 2 H, J = 8.0 Hz).
1
IR (KBr): 3278, 2930, 2100, 1592 cm .
MS-EI: m/z = 316 [M+], 274 [M – N3]+, 260, 184, 155, 91.
1H NMR (CDCl3): = 0.85 (t, 3 H, J = 7.0 Hz), 1.0–1.35 (m, 7 H),
1.37–1.60 (m, 3 H), 2.45 (s, 3 H), 3.20–3.38 (m, 3 H), 4.55 (d, 1 H,
J = 7.0 Hz), 7.35 (d, 2 H, J = 8.0 Hz), 7.80 (d, 2 H, J = 8.0 Hz).
Anal. Calcd for C15H16N4O2S (316.37): C, 56.95; H, 5.10; N, 17.71;
S, 10.13. Found: C, 56.91; H, 5.13; N, 17.8; S, 10.21.
MS-EI: m/z = 325 [M+], 282, 268, 254, 155, 91.
Anal. Calcd for C15H24N4O2S (324.43): C, 55.53; H, 7.46; N, 17.27;
S, 9.88. Found: C, 55.51; H, 7.50; N, 17.3; S, 9.90.
Synthesis 2002, No. 16, 2383–2386 ISSN 0039-7881 © Thieme Stuttgart · New York