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Imidazo-1,5-alkynyl alcohol derivatives were synthesized, and they were cyclized to imidazo-1,4-oxazines by means of cesium carbonate. Propargyl-allene isomerization was examined, and the reaction mechanism was proposed. Moreover, cytotoxicity of synthesized molecules against LN405 cell lines was investigated by means of structure-activity relationship (SAR). With SAR study, toxicities of some functional groups have been shown. In addition, two lead compounds were tested against DNA damaging. 2 of 12 | KUZU et al. 3.22 | [1-(Prop-2-yn-1-yl)-4-(thiophen-2-yl)-1H-imidazol-2-yl](thiophen-2-yl)methanol (7h) Brown solid, m.p.: 145-146°C; yield: 80%. 1 H NMR (400 MHz, d 6 -DMSO) δ = 7.57 (s, 1H, H-7), 7.47 (dd, J 15,17 = 1.26 Hz, J 15,16 = 5.05 Hz, 1H, H-15), 7.34 (dd,

N-Propargyl-2-aroylimidazoles synthesized and converted into the corresponding ketoximes. Under various conditions, several mono- and diketoxime imidazole derivatives were formed by converting the carbonyl or carbonyl and propargyl groups into oxime groups. N-Propargyl monooxime imidazole derivatives were cyclized by treatment with CuI to give various imidazopyrazine N-­oxides. Several copper salts, such as CuOAc, CuSO4, and CuOTf, formed the same cyclization product. This cyclization reaction occurred only in the presence of Cu(I) or Cu(II) salts; other transition metals such as Au, Ag, In, and Fe did not yield cyclic products. The nucleus-independent chemical shift method was used to calculate the aromaticity of the bicyclic rings.