SOMMAIRE

J.MAR.CHIM.HETEROCYCL. Volume 1, N° 1 Décembre 2002
1.7. 1-Methyl-1,4-dihydro-2H-benzo[d][1,3]oxazine-2,4-dione : 4b
Yield = 88% ; mp = 164-165°C (CH3CN) [17] ; 1 HNMR (CDCl3) δ ppm : 3.6 (s, 3H, NCH3), 7.4-7.2
(m, 2H, Harom), 7.8 (m, 1H, Harom), 8.1-8.2 (m, 1H, Harom) ; IR (KBr, cm -1 ) : 1710, 1765 ; MS
m/z (FAB positive) 178 (M+H + ).
1.8. 1-Methyl-1,4-dihydro-2H-pyrido[2,3-d][1,3]oxazine-2,4-dione : 4c
Yield = 80% ; mp = 160-162°C (CHCl3/ Cyclohexane, 1:1) ; 1 HNMR (CDCl3) δ ppm : 3.7 (s, 3H,
NCH3), 7.2-7.3 (m, 1H, Harom), 7.4-8.5 (m, 1H, Harom), 8.7-8.8 (m, 1H, Harom) ; IR (KBr, cm -1 ) :
1715, 1765 ; MS m/z (FAB positive) 179 (M+H + ).
1.9. Cis(4a,8a)-1-Methylperhydrobenzo[d][1,3]oxazine-2,4-dione : 4d
Yield = 92% ; mp = 79-80°C (Cyclohexane) ; 1 HNMR (CDCl3) δ ppm : 1.3-2.0 (m, 8H), 2.3 (m,
1H), 3.1 (s, 3H, NCH3), 3.8 (m, 1H) ; IR (KBr, cm -1 ) : 1830, 1745 ; MS m/z (FAB positive) 184
(M+H + ).
1.10. Trans(4a,8a)-1-Methylperhydrobenzo[d][1,3]oxazine-2,4-dione : 4e
Yield = 92% ; mp = 72-73°C (Cyclohexane) ; 1 HNMR ( CDCl3) δppm : 1.3-1.9 (m, 8H), 2.3 (m,
1H), 3.1 (s, 3H, NCH3), 3.8 (m, 1H) ; IR (KBr, cm -1 ) : 1830, 1740 ; MS m/z (FAB positive) 184
(M+H + ).
References
[1] M. K. Dhaon, and R. K. Olsen, J. Org. Chem., 1981, 46, 3436.
[2] B. Vitoux, A. Aubry, M. T. Cung, and M. Marraud, Int. J. Peptide Protein Res., 1986, 27, 617.
[3] M. Calmes, J. Daunis, J. Elyacoubi, and R. Jacquier, Tetrahedron Asymmetry, 1990, 1, 329.
[4] (a) H. Leuchs, Dtsch. Chem. Ges., 1906, 39, 857. (b) H. Leuchs, and W. Manasse, Ber. Dtsch.
Chem. Ges., 1907, 40, 3235.
[5] (a) R. Fuchs, Chem. Ber., 1922, 55, 2943. (b) A. C. Farthing, J. Chem. Soc., 1950, 3213. (c) A.
Patchornik, M. Sila and E. Katchalski, J. Am. Chem. Soc., 1954, 76, 299. (d) H. R.
Kricheldorf, Chem. Ber., 1970, 103, 3353.
[6] W. D. Fuller, M. S. Verlandier, and M. Goodman, Biopolymers, 1975, 15, 1869.
[7] M. Oya, R. Katakai, and H. Nakai, Chem. Lett., 1973, 1143.
[8] W. H. Daly, and D. Poche, Tetrahedron Lett., 1988, 29, 5859.
[9] R. Wilder, and S. Mobashery, J. Org. Chem., 1992, 57, 2755.
[10] S. Mobashery, and M. Johnston, J. Org. Chem., 1985, 50, 2200.
[11] (a) H. R. Kricheldorf, α-Aminoacid-N-Carboxy Anhydride and Related Heterocycles :
Springer-Verlag : Berlin, 1986, 3. (b) M. McKiernan, J. Huck, J. A. Fehrentz, M. L.
Roumestant, Ph. Viallefont and J. Martinez, J. Org. Chem., 2001, 66, 6541.
[12] (a) M Akssira, H. Kasmi, A. Dahdouh, and M. Boumzebra,. Tetrahedron Lett., 1992, 33, 1887.
(b) M Akssira, M. Boumzebra, H. Kasmi, A. Dahdouh, M. L. Roumestant, and Ph. Vialleffont,
Tetrahedron, 1994, 50, 9051.
[13] N-Methylated-Boc-aminoacids are prepared as described by S. T. Cheung, and L. Benoiton,
Can. J. Chem., 1977, 55, 906.
[14] F. Fülöp, Chem. Rev., 2001, 101, 2181 and references cited therein.
[15] M. Marastoni, R. Guerrini, G. Balboni, S. Salvadori, G. Fantin, M. Fogagnolo, L. H. Lazarus,
and R. Tomatis, Arzneim. Forsch., 1999, 49, 6.
[16] (a) H. R. Kricheldorf, Chem. Ber., 1972, 105, 3958. (b) H. R. Kricheldorf, Makromol. Chem.,
1973, 173, 13.
[17] G. E. Hardtmann, G. Koletar, and O. R. P. Fister, J. Heterocycl. Chem., 1975, 12, 565.
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