Y. Xie et al. / Tetrahedron Letters 52 (2011) 932–935
935
46, 7201; (c) Koketsu, M.; Takenaka, Y.; Ishihara, H. Heteroat. Chem. 2003, 14,
106; (d) Amosova, S. V.; Penzik, M. V.; Albanov, A. I.; Potapov, V. A. Tetrahedron
Lett. 2009, 50, 306; (e) Segi, M.; Tanno, K.; Kojima, M.; Honda, M.; Nakajima, T.
Tetrahedron Lett. 2007, 48, 2303.
mixture was evaporated under vacuum. The residue was purified by flash
chromatography on silica gel (petroleum ether/ethyl acetate, 2:1) to give 4a
(0.217 g, 85%) as white solid. Mp: 101.5–102.1 °C; IR (KBr):
mmax = 3317, 3240,
1697, 1633, 1590 cmꢀ1 1H NMR (400 MHz, DMSO-d6): d = 7.38 (t, J = 7.6 Hz,
;
8. (a) Zhou, Y. H.; Linden, A.; Heimgartner, H. Helv. Chim. Acta 2000, 83, 1576; (b)
Atanassov, P. K.; Zhou, Y. H.; Linden, A.; Heihartner, H. Helv. Chim. Acta 2002, 85,
1102; (c) López, Ó.; Maza, S.; Ulgar, V.; Maya, I.; Fernández-Bolaños, J. G.
Tetrahedron 2009, 65, 2550; (d) Fernández-Bolaños, J. G.; López, Ó.; Ulgar, V.;
Maya, I.; Fuentes, J. Tetrahedron Lett. 2004, 45, 4081.
2H, ArH), 7.16 (t, J = 7.6 Hz, 1H, ArH), 6.94 (d, J = 7.6 Hz, 2H, ArH), 5.39 (br, 2H,
NH2), 3.98 (s, 2H, CH2); 13C NMR (100 MHz, DMSO-d6): d = 169.6, 150.3, 149.2,
129.5 (CH ꢁ 2), 124.5, 120.5 (CH ꢁ 2), 23.5; MS (EI): m/z (%) = 251 (22), 253
(49), 255 (M+, 100); HRMS-ESI: calcd for C9H10N3OSe (M+H)+: 255.9989;
found: 255.9983.
9. (a) Sommen, G. L.; Linden, A.; Heimgartner, H. Eur. J. Org. Chem. 2005, 3128; (b)
Sommen, G. L.; Linden, A.; Heimgartner, H. Helv. Chim. Acta 2005, 88, 766; (c)
Garud, D. R.; Makimura, M.; Ando, H.; Ishihara, H.; Koketsu, M. Tetrahedron Lett.
2007, 48, 7764; (d) Sommen, G. L.; Linden, A.; Heimgartner, H. Lett. Org. Chem.
2007, 4, 7; (e) Garud, D. R.; Koketsu, M. Org. Lett. 2008, 10, 3319; (f) Garud, D.
R.; Toyoda, Y.; Koketsu, M. Tetrahedron Lett. 2009, 50, 3035; (g) Heimgartner,
H.; Zhou, Y.-H.; Atanassov, P. K.; Sommen, G. L. Phosphorus, Sulfur, Silicon. 2008,
180, 840.
10. (a) Sommen, G. L.; Linden, A.; Heimgartner, H. Tetrahedron 2006, 62, 3344; (b)
Koketsu, M.; Nada, F.; Ishihara, H. Synthesis 2002, 195; (c) Toyoda, Y.; Garud, D.
R.; Koketsu, M. Heterocycles 2009, 78, 449.
11. Bulka, E.; Ahlers, K. D.; Tucek, E. Chem. Ber. 1967, 100, 1373.
12. Typical procedure for the preparation of 2-imino-1,3-selenazolidin-4-ones 4
13. Typical procedure for the preparation of 2-amino-1,3,4-selenadiazin-5-ones 6
(6a was selected as example): A mixture of isoselenocyanates 1b (0.212 g,
1 mmol) and phenylhydrazine (0.108 g, 1 mmol) in CH2Cl2 (10 ml) was stirred
at room temperature until total consumption of the starting material (TLC, 1 h).
Then chloroacetic chloride (0.136 g, 1.2 mmol) was added dropwise at 0–5 °C,
and the resulting mixture was stirred at this temperature for 0.5 h. After the
completion of the reaction, the reaction mixture was evaporated under
vacuum. The residue was purified by flash on silica gel (petroleum ether/
ethyl acetate, 4:1) to give 6a (0.285 g, 86%) as faint yellow solid. Mp: 186.4–
187.1 °C; IR (KBr):
m ;
max = 3269, 1627, 1590, 1573, 1490 cmꢀ1 1H NMR
(400 MHz, DMSO-d6): d = 9.37 (s, 1H, NH), 7.56 (d, J = 8.4 Hz, 2H, ArH), 7.49
(d, J = 8. 0 Hz, 2H, ArH), 7.42 (t, J = 8.0 Hz, 2H, ArH), 7.28–7.21 (m, 3H, ArH),
6.95 (t, J = 7.6 Hz, 1H, ArH), 3.68 (s, 2H, CH2); 13C NMR (100 MHz, DMSO-d6):
d = 161.2, 144.4, 141.9, 140.7, 128.7 (CH ꢁ 2), 128.4 (CH ꢁ 2), 126.1, 124.8
(CH ꢁ 2), 122.2, 118.6 (CH ꢁ 2), 22.0; MS (ESI): m/z (%) = 330 (49), 332 (M++1,
100); HRMS-ESI: calcd for C15H14N3OSe (M+H)+: 332.0302; found: 332.0301.
14. (a) Bulka, E.; Ahlers, K. D. Z. Chem. 1963, 3, 349; (b) Stanislaw, B.; Jozef, C.;
Diwa, M.; Tadeusz, U. Acta Pol. Pharm. 1979, 36, 307; (c) Sommen, G. L.; Linden,
A.; Heimgartner, H. Helv. Chim. Acta 2006, 89, 1322.
and
5 (4a was selected as example): A mixture of isoselenocyanates 1a
(0.182 g, 1 mmol) and 85% hydrazine hydrate (0.059 g, 1 mmol) in CH2Cl2
(10 ml) was stirred at room temperature until total consumption of the
starting material (TLC, 1 h). Then ethyl chloroacetate (0.184 g, 1.5 mmol) and
triethylamine (0.101 g, 1 mmol) were added and the resulting mixture was
stirred at reflux temperature. After the completion of the reaction, the reaction