反应详情

Alkylation of oxazine alcohol 149 (see Example 2OO) with 4-iodobenzyl bromide (1.7 equiv.) and NaH (1.9 equiv.) as in Example 2UU above for 3 h, followed by chromatography of the product on silica gel, eluting with CH2Cl2 (foreruns) and then with 1% EtOAc/CH2Cl2, gave 7-{[(4-iodobenzyl)oxy]methyl}-7-methyl-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (156) (54%) as a cream solid: mp (CH2Cl2/pentane) 130-132° C.; 1H NMR (CDCl3) δ 7.67 (dt, J=8.3, 2.0 Hz, 2H), 7.39 (s, 1H), 6.99 (br d, J=8.3 Hz, 2H), 4.49 (s, 2H), 4.09 (ddd, J=12.5, 7.0, 5.9 Hz, 1H), 4.01 (ddd, J=12.5, 7.1, 5.9 Hz, 1H), 3.62 (d, J=10.2 Hz, 1H), 3.58 (d, J=10.2 Hz, 1H), 2.37 (ddd, J=14.4, 7.0, 6.0 Hz, 1H), 2.10 (ddd, J=14.4, 6.9, 6.0 Hz, 1H), 1.46 (s, 3H). Anal. (C15H16IN3O4) C, H, N.

1. customabove for 3 h
2. washeluting with CH2Cl2 (foreruns)