Abstract
Various ethyl 3,4-dihydropyrimidin-2(1H)-one-5-carboxylates were oxidized to their corresponding ethyl pyrimidin-2(1H)- one-5-carboxylates by potassium peroxydisulfate in refluxing aqueous acetonitrile. The products were obtained in good to excellent yields. The effect of the nature of 4-substituent and also the nature of solvent play an important role on the rate of oxidation.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
N. Nakamichi, Y. Kawashita, M. Hayashi, Org. Lett. 4 (2002) 3955.
N. Nakamichi, Y. Kawashita M. Hayashi, Synthesis (2004) 1015.
D.J. Brown, The pyrimidine, Interscience New York, N. Y., 1994.
K.C. Majumdar, U. Das, N.K. Jana, J. Org. Chem. 63 (1998) 3550.
R.C. Rizzo, J. Tirado-Rives, W.L. Jorgensen, J. Med. Chem. 44 (2001) 145.
W. Zhou, G. Gumina, Y. Chong, J. Wang, R.F. Schinazi, C.K. Chu, J. Med. Chem. 47 (2004) 3399.
K. Itami, D. Yamazaki, J. Yoshida, J. Am. Chem. Soc. 126 (2004) 15396.
C.O. Kappe, Acc. Chem. Res. 33 (2000) 360 and references cited therein.
C.P. Sar, O.H. Hankovszky, G. Jerkovich, I. Pallagi, K. Hideg, ACH-Models in Chemistry 131 (1994) 363.
V.A. Salvinskaya, G. Duburs, D. Sile, D. Kreile, E.L. Khanina, USSR Patent (1978) 632695; Chem. Abstr. 90 (1979) 121631y.
E.L. Khanina, G.Y. Dubur, Khim. Geterotsik. Soedin. (1982) 535.
H.R. Memarian, M. Abdoli-Senejani, Döpp, D.J. Chin. Chem. Soc. 54 (2007) 131 and references cited therein.
J.J. Vanden Eynde, N. Audiart V. Canonne, S. Michel, Y. Van Haverbeke, C.O. Kappe, Heterocycles 45 (1997) 1967.
J. Lu, Y. Bai, Z. Wany, B. Yabg, W. Li, Synth. Commun. 31 (2001) 2625.
S.H. Mashraqui, M. Kamik, Synthesis (1998) 713.
P. Shanmugam, P.T. Perumal, Tetrahedron 62 (2006) 9726.
P. Shanmugam, P.T. Perumal, Tetrahedron 63 (2007) 666.
C.A. Synder, M.A. Thorn, J.E. Klijanowicz, P.L. Southwick, J. Heterocycl. Chem. 19 (1982) 603.
R.S. Varma, D. Kumar, J. Chem. Soc. Perkin Trans. 1 (1999) 1755.
D.A. Skoog, J.J. Leary, In Principles of Instrumental Analysis, Horcourt Brace College Publishers, 1992, p. A–60.
D.A. House, Chem. Rev. 62 (1962) 185.
R.C. Moschel, E.J. Behrman, J. Org. Chem. 39 (1974) 1983.
A. Clerici, O. Porta, J. Chem. Soc. Perkin Trans. 2 (1980) 1234.
W.E. Fristad, J.R. Peterson, Tetrahedron Lett. 24 (1983) 4547.
G.I. Nikishin, E.I. Troyansky, M.I. Lazareva, Tetrahedron Lett. 25 (1984) 4987.
T. Itahara, Y. Fujii, M. Tada, J. Org. Chem. 53 (1988) 3421 and references cited therein.
S. Yamasaki, Chem. Lett. (1992) 323 and references cited therein.
C. Srinivasan, P. Kuthalingam, N. Arumugam, Can. J. Chem. 56 (1978) 3043.
H.R. Memarian, I. Mohammadpoor-Baltork, M.M. Sadeghi, Z.S. Samani, Indian J. Chem. 40B (2001) 727.
S.-C. Hsu, T.-M. Don, W.-Y. Chiu, Polymer Degradation and Stability 75 (2002) 73.
Y.S. Choi, H.T. Ham, I. Chung, J. Polymer. 44 (2003) 8147.
M.M. Khodaei, A.R. Khosropour, M. Beygzadeh, Synth. Commun. 34 (2004) 1551.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Memarian, H.R., Farhadi, A. Potassium peroxydisulfate as an efficient oxidizing agent for conversion of ethyl 3,4-dihydropyrimidin-2(1H)-one-5-carboxylates to their corresponding ethyl pyrimidin-2(1H)-one-5-carboxylates. JICS 6, 638–646 (2009). https://doi.org/10.1007/BF03246543
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF03246543