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Study on Synthesis of 2,6-Substitute Purine Derivatives

Author: LuHongFei
Tutor: LvChunXu;LuMing
School: Nanjing University of Technology and Engineering
Course: Applied Chemistry
Keywords: Purine Substitute Synthesis Fluorine Trifluoromethyl Trifluoroethoxyl Fungicidal activities
CLC: O626
Type: PhD thesis
Year: 2006
Downloads: 395
Quote: 0
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Purine derivatives are a kind of important semi-pharmic of nucleotide. During thispaper, lots of purine derivatives are synthesized from the material of guanine. Thefactors that can influence reaction are studied by the numbers.Guanine as the raw material, during the acetic acid and acetic anhydride,N2·9-diacetylguanine are prepared under the condition of 135℃, the yield is 95.6%.Through chloridization and hydrolyzation, 2-amino-6-chloropurine is prepared, then,through halogen exchanging, 2-amino-6-halogenpurine derivatives are prepared.Through the calculation of quantum chemistry by the procedure of Guass98, thereaction activity of the four purine derivatives has been come out. 2-amino-6-chloro-purine as the raw material, during the organic solvent of DMF, through alkoxylatereaction, 2-amino-6-alkoxypurine derivatives are prepared. 2-amino-6-chloropurine asthe raw material, during the organic solvent of DMF, 2-amino-6-aminogroupsubstitutepurine derivatives are prepared. 2-amino purine derivatives as the raw material, usingNaNO2, through diazotization, 2-halogenpurine derivatives are prepared. Thecalculation of quantum chemistry by the procedure of Guass98 shows that the existingof electron-donating group in C6 can make the substitution by bromine and chlorine easier andget higher yield, and it also shows that the existing of electron-acquired groups in C6can make the substitution by iodine and fluorin easier and get higher yield. 6-chloropurinederivatives as the raw material, 6-fluoropurine derivatives are prepared under thecondition of dry DMSO and dry KF. 6-bromopurine derivatives as the raw material,6-trifluoromethylpurine derivatives are prepared under the condition of dry DMF anddry NaOOCCF3 and CuI. 6-chloropurine derivatives as the raw material,trifluoroethoxylpurine derivatives are prepared under the condition of dry DMF anddry NaOH2CCF3.Bacillus subtillis, Aspergillus niger and Cardida tropical are selected to test thefungicidal activities of purine derivatives. Purine derivatives was confected tosolution of 3*10-5 g/mL by sodium hydroxide solution(1 weight% in water), and thenmeasured the diameter of fungistatic circle.

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