Citation: YU Yun, HE Jia-Xin, HU Hui-Ling, LIN Zhi-Lan, GAO Yuan. Efficient Synthesis, Crystal Structure and Antibacterial Activity of Two Novel 1,3-Oxazin Derivatives[J]. Chinese Journal of Structural Chemistry, ;2014, 33(3): 441-447. shu

Efficient Synthesis, Crystal Structure and Antibacterial Activity of Two Novel 1,3-Oxazin Derivatives

1.
College of Chemistry and Chemical Engineering, Shenzhen University, Shenzhen 518060, China

Corresponding author: GAO Yuan,
Received Date: 13 August 2013
Available Online: 22 September 2013
Fund Project: Project supported by the National Natural Science Foundation of China (No. 81071144) (No. 81071144)Natural Science Foundation of Guangdong Province (No. 9451806001002961) (No. 9451806001002961)

Two new 1,3-oxazin derivatives, C₂₂H₂₄N₂O₅ (3I) and C₁₉H₁₆N₂O₅ (3Ⅱ), have been synthesized via an unusual cascade reaction. The attractive aspect of this cascade reaction is that the novel construction of 1,3-oxazine and the direct C-N bond formation from C-C bond can be easily achieved via pyridine-mediated acylation in a one-pot operation. Both compounds have been synthesized and characterized by elemental analysis, IR, NMR spectra and X-ray single-crystal diffraction. Compound 3I crystallizes in monoclinic, space group P2₁/n with a=16.282(4), b=7.4117(18), c=17.256(5) Å, β=103.193(9)°, V=2027.4(9) Å³, M_r=396.43, Z=4, D_c=1.299 g/cm³, F(000)=840, MoKa radiation (λ=0.71073 Å), the final R=0.0771 and wR=0.1582 for 3662 were observed reflections with I>2σ(I). Compound 3Ⅱ crystallizes in triclinic, space group P1 with a=7.1265(9), b=10.1071(13), c=23.529(3) Å, α=97.463(9), β=96.981(9), γ=94.345(9)°, V=1600.5(4) Å³, Z=4, D_c=1.409 g/cm³, F(000)=736, CuKa radiation (λ=1.54186 Å), the final R=0.0515 and wR=0.1241 for 4920 observed reflections with I>2σ(I). The preliminary antibacterial activities of 2 and 3 against E. coli and S. aureus were investigated. The results showed that the inhibiting effect of 3 was higher than that of 2.
- pyrane,
- 1,3-oxazin,
- synthesis,
- crystal structure,
- antibacterial activity
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