The dry residue
was dissolved in CHCl3 and purified by column chromatography (aluminum oxide, CHCl3) to give 10H-1,find more 8-diazaphenothiazine (4) (0.088 g, 88 %) Synthesis of 10-substituted 1,8-diazaphenothiazines 7, 8, and 10–12 To a solution of 10H-1,8-diazaphenothiazine (4) (0.100 g, 0.5 mmol) in dry DMF (5 ml) NaH (0.024 g, 1 mmol, 60 % NaH in mineral oil was washed out with hexane) was added. The reaction mixture was stirred at room temperature for 1 h and then alkyl, aryl, and heteroaryl halides (methyl iodide, allyl bromide, benzyl chloride, 1-fluoro-4-nitrobenzene, 4-chloro-3-pyridine, 1.5 mmol) were added and the stirring was continued for 24 h. The mixture was poured into water (15 ml), extracted with CHCl3 (3 × 10 ml), and dried using Na2SO4. The obtained product was purified by Adriamycin column chromatography (aluminum oxide, CHCl3) to Selleck MK1775 give 10-Methyl-1,8-diazaphenothiazine (7) (0.085 g, 79 %); mp 82–83 °C 1H NMR (CDCl3) δ 3.44 (s, 3H, CH3), 6.90 (dd, J = 7.2 Hz, J = 4.9 Hz, 1H, H3), 7.18 (d, J = 5.4 Hz, 1H, H6), 7.26 (dd, J = 7.8 Hz, J = 1.8 Hz, 1H, H4), 7.90 (s, 1H, H9), 8.07 (d, J = 5.4 Hz, 1H, H7), 8.09 (dd, J = 4.9 Hz, J = 1.8 Hz, 1H, H2). 13C NMR (CDCl3) δ 32.8 (NCH3),
115.0 (C4a), 118.2 (C3), 120.8 (C6), 131.9 (C5a), 134.4 (C4), 135.2 (C9), 139.9 (C9a), 143.9 (C7), 145.8 (C2), 154.3 (C10a). EI MS m/z: 215 (M, 100), 200 (M-CH3, 80). Anal. Calcd for: C11H9N3S C 61.37, H 4.21, N 19.52. Found: C 61.22; H 4.23; N 19.41. 10-Allyl-1,8-diazaphenothiazine (8) (0.085 g, 70 %);
an oil 1H NMR (CDCl3) δ 4.66 (m, 2H, N-CH2), 5.32 (m, 2H, =CH2), 5.96 (m, 1H, CH), 6.82 N-acetylglucosamine-1-phosphate transferase (dd, J = 7.5 Hz, J = 5.1 Hz, 1H, H3), 7.04 (d, J = 5.0 Hz, 1H, H6), 7.18 (dd, J = 7.5 Hz, J = 1.5 Hz, 1H, H4), 7.89 (s, 1H, H9), 8.02 (m, 2H, H2, H7). 13C NMR (CDCl3) δ 47.6 (NCH2), 113.0 (C4a), 118.1 (C3), 119.2 (C6), 121.1 (CH2=), 130.2 (C5a), 131.2 (C4), 134.5 (C9), 137.9(–CH=), 138.8 (C9a), 140.2 (C7), 146.4 (C2), 151.9 (C10a). EI MS m/z: 241 (M, 50), 200 (M-CH2CHCH2, 100). Anal. Calcd for: C13H11N3S C 64.70, H 4.59, N 17.41. Found: 64.58; H 4.58; N 17.31. 10-Benzyl-1,8-diazaphenothiazine (10) (0.095 g, 65 %); an oil 1H NMR (CDCl3) δ 5.34 (s, 2H, CH2), 6.76 (dd, J = 7.2 Hz, J = 4.8 Hz, 1H, H3), 6.87 (d, J = 5.0 Hz, 1H, H6), 7.22 (dd, J = 7.2 Hz, J = 1.4 Hz, 1H, H4), 7.29 (m, 5H, C6H5), 7.81 (s, 1H, H9), 7.96 (m, 2H, H2, H7). EI MS m/z: 291 (M, 80), 200 (M-CH2C6H5, 100).