1018
Russ.Chem.Bull., Int.Ed., Vol. 60, No. 5, May, 2011
Obydennov et al.
97.51 (CH=); 100.01 (CH=); 142.22 (C(5)); 160.00 (C(2));
165.74 (CO); 166.24 (CO). MS, m/z (Irel (%)): 354 [M]+ (100).
Found (%): C, 44.1; H, 2.9; N, 7.9; S, 18.0. C13H10N2O6S2.
Calculated (%): C, 44.06; H, 2.84; N, 7.91; S, 18.10.
3. M. F. Kosterina, Yu. Yu. Morzherin, A. V. Tkachev, T. V.
Rybalova, Yu. V. Gatilov, V. A. Bakulev, Izv. Akad. Nauk,
Ser. Khim., 2002, 604 [Russ. Chem. Bull., Int. Ed., 2002,
51, 653].
3ꢀCyclohexylꢀ5ꢀethoxycarbonylmethylideneꢀ2ꢀ[(5ꢀethoxyꢀ
carbonylmethylideneꢀ4ꢀoxoꢀ4,5ꢀdihydrothiazolꢀ2ꢀyl)methylidꢀ
ene]thiazolidinꢀ4ꢀone (3) was obtained similarly from thioamide
1b (0.61 g, 3 mmol) and diethyl acetylenedicarboxylate. The
4. K. A. Volkova, A. S. Nakhmanovich, V. N. Elokhina, T. I.
Yaroshenko, L. I. Larina, A. M. Shulunova, S. V. Amosova,
Zh. Org. Khim., 2007, 43, 770 [Russ. J. Org. Chem. (Engl. Transl.),
2007, 43, 768].
5. T. V. Nizovtseva, T. N. Komarova, A. S. Nakhmanovich,
L. I. Larina, V. A. Lopyrev, E. F. Kaistratova, Zh. Org. Khim.,
2002, 38, 1256 [Russ. J. Org. Chem. (Engl. Transl.), 2002,
38, 1205].
6. V. N. Elokhina, T. I. Yaroshenko, A. S. Nakhmanovich,
L. I. Larina, S. V. Amosova, Zh. Obshch. Khim., 76, 2006,
2005 [Russ. J. Gen. Chem. (Engl. Transl.), 2002, 76, 1916].
7. T. V. Nizovtseva, T. N. Komarova, A. S. Nakhmanovich,
V. A. Lopyrev, Khim. Geterotsikl. Soedin., 2002, 1293 [Chem.
Heterocycl. Compd. (Engl. Transl.), 2002, 38, 1134].
8. T. E. Glotova, A. S. Nakhmanovich, A. I. Albanov, N. I.
Protsuk, T. V. Nizovtseva, V. A. Lopyrev, Khim. Geterotsikl.
Soedin., 2002, 81 [Chem. Heterocycl. Compd. (Engl. Transl.),
2002, 38, 74].
9. T. V. Nizovtseva, T. N. Komarova, A. S. Nakhmanovich,
Zh. Org. Khim., 2007, 43, 142 [Russ. J. Org. Chem. (Engl. Transl.),
2007, 43, 148].
10. H. Lehr, W. Guex, H. Erlenmeyer, Helv. Chim. Acta, 1944,
27, 971.
11. W. Whitehead, J. Traverso, J. Am. Chem. Soc., 1955, 77, 5872.
12. N. Shobana, P. Yeshoda, P. Shanmugam, Tetrahedron, 1989,
45, 757.
1
yield was 0.89 g (68%), m.p. 165 °C. H NMR (DMSOꢀd6), δ:
1.28 (m, 7 H, 2 CH3, Hcy); 1.46—1.40 (m, 2 H, Hcy); 1.84—1.63
(m, 5 H, Hcy); 2.32—2.21 (m, 2 H, Hcy); 4.28 (q, 4 H, 2 OCH2,
J = 7.1 Hz); 4.40—4.29 (m, 1 H, Hcy); 6.78 (s, 1 H, CH); 6.85
(s, 1 H, CH); 7.15 (s, 1 H, CH). MS, m/z (Irel (%)): 464 [M]+
(25.58). Found (%): C, 54.3; H, 5.2; N, 5.9; S, 13.6. C21H24N2O6S2.
Calculated (%): C, 54.29; H, 5.21; N, 6.03; S, 13.80.
5ꢀMethoxycarbonylmethylideneꢀ3ꢀ(4ꢀmethoxyphenyl)ꢀ2ꢀ
{[Nꢀ(4ꢀmethoxyphenyl)thiocarbamoyl]methylidene}thiazolidinꢀ4ꢀ
one (4). Dimethyl acetylenedicarboxylate (0.364 mL, 3.0 mmol)
was added to a solution of malonodithioamide 1c (1.04 g,
3.0 mmol) in acetone (50 mL) at 0 °C with stirring. The reaction
mixture was stirred at this temperature for 3 h, then kept for 48 h
at –20 °C. A precipitate was filtered off and recrystallized from
EtOH. The yield was 0.62 g (45%), m.p. 130 °C. 1H NMR
(DMSOꢀd6), δ: 3.76 (s, 3 H, CH3O); 3.83 (s, 3 H, CH3O); 3.87
(s, 3 H, CH3O); 6.18 (s, 1 H, CH); 6.66 (s, 1 H, CH); 6.85
(d, 2 H, Ar, J = 9.0 Hz); 7.15 (d, 2 H, Ar, J = 9.0 Hz); 7.31
(d, 2 H, Ar, J = 9.0 Hz); 7.58 (d, 2 H, Ar, J = 9.0 Hz); 11.15
(s, 1 H, NH). MS, m/z (Irel (%)): 456 [M]+ (33). Found (%):
C, 57.88; H, 4.42; N, 6.14; S, 14.05. C22H20N2O5S2. Calculatꢀ
ed (%): C, 57.88; H, 4.22; N, 6.14; S, 14.05.
13. H. Becker, W. Berger, G. Domschke, E. Fanghänel, J. Faust,
M. Fishcer, F. Gentz, K. Gewald, R. Gluch, R. Mayer,
K. Müller, D. Pavel, H. Schmidt, K. Schollberg, K. Schwetꢀ
lick, E. Seiler, G. Zeppenfeld, Organikum, WILEYꢀVCH,
Weinheim, 2001, 852 pp.
References
1. V. S. Berseneva, A. V. Tkachev, Yu. Yu. Morzherin, W. Deꢀ
haen, I. Luyten, S. Toppet, V. A. Bakulev, J. Chem. Soc.,
Perkin Trans. 1, 1998, 2133.
2. V. A. Bakulev, V. S. Berseneva, N. P. Belskaia, Yu. Yu.
Morzherin, A. Zaitsev, W. Dehaen, I. Luyten, S. Toppet,
Org. Biomol. Chem., 2003, 134.
14. G. Barnikow, V. Kath, D. Richter, J. Prakt. Chem., 1965,
30, 63.
Received February 11, 2011;
in revised form April 13, 2011