Abstract
A series of 1,3-oxazin-6-one derivatives has been synthesized upon treatment of N-unsubstituted amides with chlorocarbonyl phenyl ketene under reflux in toluene for several minutes. In this simple way, 2,5-disubstituted derivatives of 1,3-oxazin-6-ones have been obtained in high yields.
References
D. L. Boger, Tetrahedron, 1983, 39, 2869.
A. Krantz, B. Hoppe, J. Am. Chem. Soc., 1975, 97, 6590.
H. McNab, K. Withell, Tetrahedron, 1996, 52, 3163.
H. Sheibani, P. V. Bernhardt, C. Wentrup, J. Org. Chem., 2005, 70, 5859.
W. Ried, H. Nenninger, Synthesis, 1990, 167.
K. T. Potts, M. O. Dery, R. K. Kullnig, J. Chem. Soc., Chem. Commun., 1987, 840.
K. Saidi, H. Sheibani, Synth. Commun., 2001, 31, 1809.
H. Sheibani, D. Lari, M. Islami, K. Saidi, Izv. Akad. Nauk, Ser. Khim., 2003, 1335 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1411].
H. Sheibani, M. R. Islami, H. Khabazzadeh, K. Saidi, Tetrahedron, 2004, 60, 5931.
H. Sheibani, M. H. Mosslemin, S. Behzadi, M. R. Islami, K. Saidi, Synthesis, 2006, 3, 435.
H. Sheibani, M. H. Mosslemin, S. Behzadi, M. R. Islami, H. Foroughi, K. Saidi, ARKIVOC, 2005, 15, 88.
L. George, R. N. Veedu, H. Sheibani, A. A. Taherpour, R. Flammang, C. Wentrup, J. Org. Chem., 2007, 72, 1399.
W. Stadlbauer, E1-S. Badawey, C. Hojas, P. Roschger, T. Kappe, Molecules, 2001, 6, 338.
S. Nakanishi, K. Butler, Org. Prep. Proced. Int., 1975, 7, 155.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2549–2551, December, 2008.
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Sheibani, H., Saidi, K. & Foroughi, H. Studies on condensation of chlorocarbonyl phenyl ketene with N-unsubstituted amides: synthesis of some new 1,3-oxazin-6-ones. Russ Chem Bull 57, 2600–2602 (2008). https://doi.org/10.1007/s11172-008-0374-3
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DOI: https://doi.org/10.1007/s11172-008-0374-3