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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 29, 1999 - Issue 24
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Original Articles

Self Condensation of Methyl Acetopyruvate in the Presence of 1,4-Diazabicyclo[2.2.2]Octane

Hong Jung LeeDepartment of Chemistry, Chonnam National University, Kwangju, 500-757, Korea
,
Tae Yi KimDepartment of Chemistry, Chonnam National University, Kwangju, 500-757, Korea
&
Jae Nyoung KimDepartment of Chemistry, Chonnam National University, Kwangju, 500-757, Korea
Pages 4375-4379 | Received 08 Mar 1999, Published online: 25 Sep 2007

References

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  • Rafel, S., and Leahy, J. W., 1997. J. Org. Chem. 62 (1997), p. 1521.
  • Patent number German Patent 2155113, (Chem. Abstr. 1972, 77, 34174q).
  • Drewes, S. E., and Roos, G. H. P., 1988. Tetrahedron 44 (1988), p. 4653.
  • Basavaiah, D., Rao, P. D., and Hyma, R. S., 1996. Tetrahedron 52 (1996), p. 8001.
  • Basavaiah, D., Bharathi, T. K., and Gowriswari, V. V. L., 1987. Tetrahedron Lett. 28 (1987), p. 4351.
  • Kim, J. N., and Ryu, E. K., 1990. Heterocycles 31 (1990), p. 663.
  • Song, H. N., Son, J. S., Seong, M. R., and Kim, J. N., 1998. Synth. Commun. 28 (1998), p. 687.
  • , Spectroscopic data of 2 : mp 132–134 °C; IR (KBr) 3452 (b), 2955 (w), 1760 (s), 1736 (m), 1626 (m), 1596 (s), 1442 (m), 1289 (m), 1072 (m) cm-11H NMR (DMSO-d6) δ 1.99 (s, 3H), 2.16 (s, 3H), 3.03 (s, 12H), 3.28 (dd, J = 199.0 and 17.1 Hz, 2H), 3.51 (s, 3H); 13C NMR (DMSO-d6) δ 27.89, 30.78, 44.12 (DABCO), 46.42, 52.14, 81.63, 112.48, 162.56, 170.54, 172.00, 189.09, 204.72; Mass (70 eV) m/z (rel intensity) 43 (92), 44 (100), 46 (85), 56 (100), 57 (100), 58 (100), 59 (82), 112 (DABCO, 100), 113 (66), 256 (tetrahydrofuran-2,3-dione, 2); FAB-MS 369 (M++l); Anal. Calcd for C17H24N2O7.1/2 H2O: C, 54.11; H, 6.68; N, 7.42. Found: C, 54.38; H, 6.50; N, 7.13.
  • , Spectroscopic data of 1 : mp 72–74 °C; IR (KBr) 3415 (b), 2955 (w), 1748 (s), 1699 (s), 1672 (s), 1437 (m), 1361 (m), 1237 (m) cm-11H NMR (DMSC-d6) δ 2.07 (s, 3H), 2.38 (s, 3H), 3.43 (dd, J = 134.7 and 18.0 Hz, 2H), 3.63 (s, 3H); 13C NMR (DMSO-de) δ 30.06, 30.86, 44.13, 53.44, 82.31, 122.73, 150.32, 167.90, 168.22, 192.38, 204.00; FAB-MS 257 (M++1).

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