Citation: LI Rong-Kun, YANG Quan-Li, HUANG Nian-Yu, CHEN Hong, LIU Ming-Guo. Efficient Synthesis, Crystal Structure and Antibacterial Activity of Two Novel Thieno[2,3-d]pyrimidin-4(3H)-one Derivatives[J]. Chinese Journal of Structural Chemistry, ;2015, 34(5): 673-680. doi: 10.14102/j.cnki.0254-5861.2011-0617 shu

Efficient Synthesis, Crystal Structure and Antibacterial Activity of Two Novel Thieno[2,3-d]pyrimidin-4(3H)-one Derivatives

1.
Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, China

Corresponding author: CHEN Hong, LIU Ming-Guo,
Received Date: 26 December 2014
Available Online: 5 March 2015
Fund Project: Supported by the National Natural Science Foundation of China (No.21102084) (No.21102084) Natural Science Foundation (No.KJ2010B001) (No.KJ2010B001)Scientific Research Innovation Foundation of Graduate School of China Three Gorges University (No.2011CX052) (No.2011CX052)

Two new thieno[2,3-d]pyrimidin-4(3H)-one derivatives, C₂₄H₂₂ClN₃O₂S (5a) and C₂₅H₂₅N₃O₂S (5b), have been synthesized via a tandem aza-Wittig reaction. This tandem reaction has many attractive aspects such as easily accessible and versatile starting materials, mild conditions and high yields. Both compounds have been characterized by elemental analysis, HR-MS, IR, NMR spectra and X-ray single-crystal diffraction. Compound 5a crystallizes in monoclinic, space group P2₁/c with a=9.986(3), b=14.263(4), c=15.530(5) Å, β=93.806(5)°, V=2207.1(11) Å³, M_r=451.96, Z=4, D_c=1.360 g/cm³, F(000)=944, μ=0.294 mm⁻¹, MoKα radiation (λ=0.71073 Å), the final R=0.0444 and wR=0.1219 for 3407 observed reflections with I>2σ(I). Compound 5b crystallizes in triclinic, space group P1 with a=8.974(4), b=10.766(5), c=12.260(6) Å, β=93.047(7)°, V=1122.1(9) Å³, M_r=431.54, Z=2, D_c=1.277 g/cm³, F(000)=456, μ=0.170 mm−1, MoKα radiation (λ=0.71073 Å), the final R=0.0378 and wR=0.1072 for 3806 observed reflections with I>2σ(I). The preliminary antibacterial activities of 5a and 5b were investigated. Compound 5a showed 71.3% and 79.2% in vitro inhibition against Fusarium oxysporium and Rhizoctonia solani, respectively. Compound 5b showed 75.3% in vitro inhibition against Rhizoctonia solani.
- crystal structure,
- thieno[2,3-d]pyrimidinone,
- aza-Wittig reaction,
- synthesis,
- antibacterial activity
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