2994
J.-Q. Weng et al.
Paper
Synthesis
3-Butyl-5-methylenethiazolidine-2-thione (2d)
1H NMR (500 MHz, CDCl3): δ = 5.27–5.17 (m, 2 H), 5.07 (dd, J = 4.8, 2.7
Hz, 1 H), 4.65 (t, J = 2.6 Hz, 2 H), 2.07–1.96 (m, 2 H), 1.81–1.48 (m, 6
H).
13C NMR (125 MHz, CDCl3): δ = 193.1, 136.7, 104.5, 58.6, 57.3, 28.4,
23.7.
Pale yellow liquid; yield: 74 mg (79%).
1H NMR (500 MHz, CDCl3): δ = 5.20 (q, J = 2.3 Hz, 1 H), 5.10 (dd, J = 4.8,
2.7 Hz, 1 H), 4.71 (t, J = 2.6 Hz, 2 H), 3.83–3.76 (m, 2 H), 1.72–1.63 (m,
2 H), 1.44–1.35 (m, 2 H), 0.97 (t, J = 7.4 Hz, 3 H).
HRMS (EI+): m/z [M]+ calcd for C8H13NS2: 199.0489; found: 199.0486.
13C NMR (125 MHz, CDCl3): δ = 193.5, 136.7, 104.5, 62.0, 48.5, 28.7,
20.0, 13.7.
3-Cyclohexyl-5-methylenethiazolidine-2-thione (2k)
HRMS (EI+): m/z [M]+ calcd for C8H13NS2: 187.0489; found: 187.0494.
White solid; yield: 84 mg (79%); mp 106–108 °C.
3-Isobutyl-5-methylenethiazolidine-2-thione (2e)
1H NMR (500 MHz, CDCl3): δ = 5.22 (q, J = 2.3 Hz, 1 H), 5.09 (dd, J = 4.8,
2.7 Hz, 1 H), 4.79 (m, J = 11.5, 3.7 Hz, 1 H), 4.65 (t, J = 2.6 Hz, 2 H),
1.97–1.83 (m, 4 H), 1.76–1.70 (m, 1 H), 1.50–1.33 (m, 4 H), 1.20–1.09
(m, 1 H).
13C NMR (125 MHz, CDCl3): δ = 192.6, 137.3, 104.4, 57.6, 57.3, 29.8,
25.4, 25.3.
Pale yellow liquid; yield: 68 mg (73%).
1H NMR (500 MHz, CDCl3): δ = 5.22–5.19 (m, 1 H), 5.10 (dd, J = 4.7, 2.3
Hz, 1 H), 4.71 (t, J = 2.5 Hz, 2 H), 3.63 (d, J = 7.7 Hz, 2 H), 2.17 (dp, J =
13.8, 6.9 Hz, 1 H), 0.98 (d, J = 6.7 Hz, 6 H).
13C NMR (125 MHz, CDCl3): δ = 194.3, 136.7, 104.5, 62.7, 55.8, 27.1,
20.0.
HRMS (EI+): m/z [M]+ calcd for C10H15NS2: 213.0646; found: 213.0648.
HRMS (EI+): m/z [M]+ calcd for C8H13NS2: 187.0489; found: 187.0490.
(Z)-3-Benzyl-5-benzylidenethiazolidine-2-thione (2m)
Yellow solid; yield: 96 mg (65%); mp 139–141 °C.
3-sec-Butyl-5-methylenethiazolidine-2-thione (2f)
1H NMR (500 MHz, CDCl3): δ = 7.44–7.34 (m, 7 H), 7.27 (d, J = 8.4 Hz, 1
H), 7.22 (d, J = 7.4 Hz, 2 H), 6.42 (t, J = 2.2 Hz, 1 H), 5.08 (s, 2 H), 4.77
(d, J = 2.3 Hz, 2 H).
13C NMR (125 MHz, CDCl3): δ = 193.7, 135.2, 134.6, 129.1, 128.7,
128.4, 128.3, 127.8, 127.5, 127.3, 119.4, 62.7, 51.8.
Pale yellow liquid; yield: 52 mg (56%).
1H NMR (500 MHz, CDCl3): δ = 5.24 (dd, J = 4.5, 2.4 Hz, 1 H), 5.11 (dd,
J = 4.8, 2.7 Hz, 1 H), 5.09–5.01 (m, 1 H), 4.59 (qt, J = 16.3, 2.6 Hz, 2 H),
1.69–1.55 (m, 2 H), 1.24 (d, J = 6.8 Hz, 3 H), 0.94 (t, J = 7.4 Hz, 3 H).
13C NMR (125 MHz, CDCl3): δ = 193.5, 137.0, 104.5, 77.3, 77.0, 76.8,
56.3, 54.7, 27.2, 17.1, 10.8.
HRMS (EI+): m/z [M]+ calcd for C17H15NS2: 297.0646; found: 297.0650.
HRMS (EI+): m/z [M]+ calcd for C8H13NS2: 187.0489; found: 187.0492.
(Z)-5-Benzylidene-3-propylthiazolidine-2-thione (2n)
Pale yellow liquid; yield: 97 mg (78%).
5-Methylene-3-octylthiazolidine-2-thione (2g)
1H NMR (500 MHz, CDCl3): δ = 7.38 (t, J = 7.7 Hz, 2 H), 7.26 (dd, J =
12.1, 8.2 Hz, 3 H), 6.49 (t, J = 2.1 Hz, 1 H), 4.91 (d, J = 2.0 Hz, 2 H), 3.88–
3.73 (m, 2 H), 1.77 (dd, J = 15.0, 7.5 Hz, 2 H), 1.00 (t, J = 7.4 Hz, 3 H).
13C NMR (125 MHz, CDCl3): δ = 192.8, 135.3, 128.7, 127.8, 127.8,
127.4, 119.1, 63.6, 50.1, 20.1, 11.2.
Pale yellow liquid; yield: 90 mg (74%).
1H NMR (500 MHz, CDCl3): δ = 5.20 (q, J = 2.3 Hz, 1 H), 5.10 (dd, J = 4.8,
2.7 Hz, 1 H), 4.71 (t, J = 2.6 Hz, 2 H), 3.80–3.75 (t, 2 H), 1.72–1.63 (m, 2
H), 1.41–1.20 (m, 10 H), 0.88 (t, J = 7.0 Hz, 3 H).
13C NMR (125 MHz, CDCl3): δ = 193.5, 136.7, 104.5, 62.0, 48.8, 31.8,
29.2, 29.1, 26.7, 26.6, 22.6, 14.1.
HRMS (EI+): m/z [M]+ calcd for C13H15NS2: 249.0646; found: 249.0642.
HRMS (EI+): m/z [M]+ calcd for C12H21NS2: 243.1115; found: 243.1118.
(Z)-5-Benzylidene-3-isopropylthiazolidine-2-thione (2o)
Yellow solid; yield: 93 mg (75%); mp 96–98 °C.
5-Methylene-3-phenethylthiazolidine-2-thione (2h)16
1H NMR (500 MHz, CDCl3): δ = 7.37 (t, J = 7.7 Hz, 2 H), 7.25 (t, J = 8.9
Hz, 3 H), 6.53 (t, J = 2.2 Hz, 1 H), 5.24 (dt, J = 13.6, 6.8 Hz, 1 H), 4.82 (d,
J = 2.3 Hz, 2 H), 1.30 (d, J = 6.8 Hz, 6 H).
13C NMR (125 MHz, CDCl3): δ = 191.9, 135.4, 128.7, 128.1, 127.8,
127.4, 119.3, 58.0, 49.3, 19.4.
White solid; yield: 96 mg (82%); mp 92–93 °C.
1H NMR (500 MHz, CDCl3): δ = 7.35 (dd, J = 10.4, 4.4 Hz, 2 H), 7.29–
7.25 (m, 3 H), 5.10 (q, J = 2.3 Hz, 1 H), 5.06 (dd, J = 4.9, 2.7 Hz, 1 H),
4.49 (t, J = 2.6 Hz, 2 H), 4.05–3.94 (m, 2 H), 3.08–3.03 (m, 2 H).
13C NMR (125 MHz, CDCl3): δ = 193.7, 138.0, 136.6, 128.9, 128.8,
126.9, 104.5, 63.0, 50.4, 32.7.
HRMS (EI+): m/z [M]+ calcd for C13H15NS2: 249.0646; found: 249.0649.
MS (EI): m/z calcd for C12H13NS2: 235.37, found: 235.9.
(Z)-5-Benzylidene-3-octylthiazolidine-2-thione (2p)
Pale yellow liquid; yield: 108 mg (68%).
3-Cyclopropyl-5-methylenethiazolidine-2-thione (2i)
1H NMR (500 MHz, CDCl3): δ = 7.38 (t, J = 7.7 Hz, 2 H), 7.31– 7.20 (m, 3
H), 6.48 (s, 1 H), 4.90 (d, J = 2.0 Hz, 2 H), 3.86–3.74 (m, 2 H), 1.78–1.68
(m, 2 H), 1.37–1.27 (m, 10 H), 0.90 (t, J = 6.9 Hz, 3 H).
13C NMR (125 MHz, CDCl3): δ = 192.5, 135.3, 128.7, 127.8, 127.7,
127.3, 119.1, 63.6, 48.6, 31.7, 29.2, 29.1, 26.7, 26.6, 22.6, 14.0.
Pale yellow liquid; yield: 59 mg (69%).
1H NMR (500 MHz, CDCl3): δ = 5.19 (q, J = 2.3 Hz, 1 H), 5.06 (dd, J = 4.8,
2.7 Hz, 1 H), 4.61 (t, J = 2.6 Hz, 2 H), 3.14–3.08 (m, 1 H), 1.01–0.85 (m,
4 H).
13C NMR (125 MHz, CDCl3): δ = 195.6, 137.3, 104.7, 62.2, 31.4, 6.9.
HRMS (EI+): m/z [M]+ calcd for C7H9NS2: 171.0176; found: 171.0176.
HRMS (EI+): m/z [M]+ calcd for C18H25NS2: 319.1428; found: 319.1432.
(Z)-3-Benzyl-5-ethylidenethiazolidine-2-thione (2q)
3-Cyclopentyl-5-methylenethiazolidine-2-thione (2j)
Pale yellow liquid; yield: 73 mg (62%).
Pale yellow liquid; yield: 75 mg (75%).
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2015, 47, 2991–2996