6 T. L. Gilchrist and J. E. Wood, in Comprehensive Heterocyclic Chem-
istry II, vol 6, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven,
Pergamon, Oxford, UK, 1996, p. 279–299.
7 Previous synthesis of 4-amino-1,2-oxazin-3-ones: (a) K. Tabei,
E. Kawashima and T. Kato, Chem. Pharm. Bull., 1979, 27, 1842;
(b) C. Luethy, J. Schaetzer and A. Edmunds, Pat., WO 2001066522,
2001.
8 Typical examples of the radical addition–cyclisation for heterocycle
synthesis: (a) T. Naito, Y. Honda, O. Miyata and I. Ninomiya,
J. Chem. Soc., Perkin Trans. 1, 1995, 19; (b) O. Miyata, Y. Ozawa,
I. Ninomiya and T. Naito, Tetrahedron, 2000, 56, 6199;
(c) O. Miyata, A. Nishiguchi, I. Ninomiya, K. Aoe, K. Okamura and
T. Naito, J. Org. Chem., 2000, 65, 6922; (d ) O. Miyata, K. Muroya,
T. Kobayashi, R. Yamanaka, S. Kajisa, J. Koide and T. Naito,
Tetrahedron, 2002, 58, 4459; (e) T. Kiguchi, K. Tajiri, I. Ninomiya
and T. Naito, Tetrahedron, 2000, 56, 5819; ( f ) H. Miyabe,
M. Torieda, K. Inoue, K. Tajiri, T. Kiguchi and T. Naito, J. Org.
Chem., 1998, 63, 4397; H. Miyabe, M. Ueda, K. Fujii, A. Nishimura
and T. Naito, J. Org. Chem., 2003, 68, 5618; (g) H. Miyabe,
H. Tanaka and T. Naito, Chem. Pharm. Bull., 2004, 52, 74.
9 A. L. J. Beckwith, Tetrahedron, 1981, 37, 3073.
silyloxy ester which was subjected to cyclisation using the
Breckpot reaction15 to give the desired β-lactam 10.
In conclusion, we have developed for the first time radical
addition–cyclisation of α,β-unsaturated hydroxamates contain-
ing an oxime ether for the synthesis of amino-1,2-oxazinones.
Furthermore, our novel method would provide a practical
synthesis of unnatural β-amino acid derivatives that could be
subjected to biological evaluation.
Acknowledgements
We thank Grant-in Aids for Scientific Research on Priority
Areas (A) from the Ministry of Education, Culture, Sports,
Science and Technology (T.N.) and for Scientific Research (C)
from the Japanese Society for the Promotion of Science (O.M.).
Our thanks are also directed to the Science Research Promotion
Fund of the Japan Private School Promotion Foundation for
research grant.
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O r g . B i o m o l . C h e m . , 2 0 0 4 , 2, 1 2 7 4 – 1 2 7 6
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