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

摘要

Two new thieno[2,3-d]pyrimidin-4(3H)-one derivatives,C24H22 Cl N3O2S(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)?,β = 93.806(5)o,V = 2207.1(11) ?3,Mr = 451.96,Z = 4,Dc = 1.360 g/cm3,F(000) = 944,μ = 0.294 mm-1,Mo Kα radiation(λ = 0.71073 ?),the final R = 0.0444 and w R = 0.1219 for 3407 observed reflections with I > 2σ(I).Compound 5bcrystallizes in triclinic,space group P1 with a = 8.974(4),b = 10.766(5),c = 12.260(6) ?,β = 93.047(7)o,V = 1122.1(9) ?3,Mr = 431.54,Z = 2,Dc = 1.277 g/cm3,F(000) = 456,μ = 0.170 mm-1,Mo Kα radiation(λ = 0.71073 ?),the final R = 0.0378 and w R = 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.