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http://dx.doi.org/10.5012/jkcs.2010.54.4.429

Synthesis of Some Biologically Active Halogenopurines  

Hu, Yu Lin (Chemical Engineering College, Nanjing University of Science and Technology)
Liu, Xiang (Chemical Engineering College, Nanjing University of Science and Technology)
Lu, Ming (Chemical Engineering College, Nanjing University of Science and Technology)
Ge, Qiang (Chemical Engineering College, Nanjing University of Science and Technology)
Liu, Xiao Bin (Chemical Engineering College, Nanjing University of Science and Technology)
Publication Information
Journal of the Korean Chemical Society / v.54, no.4, 2010 , pp. 429-436 More about this Journal
Abstract
A series of some biologically active halogenopurines were synthesized from commercially available guanine (1). The reaction of guanine with acetic anhydride yielded 2,9-diacetylguanine (2-1) by acetylation reaction. Further treatment of 2-1 with $POCl_3$ by PEG-2000 phase transfer catalysis furnished the important compound 3a, then 2-amino-6-halogenopurines (3b-d) were obtained through chlorine-exchange halogenations between KX and 3a by TPPB phase transfer catalyst. Further, 2-halogenopurines (2-2a-d, 4-2a-d, 5a-d) were efficiently prepared from 2-amino-6-substituted purines (1, 3a, 4-1) via a diazotization catalyzed by their corresponding CuX, and some new compounds 2-2a, 2-2c, 2-2d, 4-2c, 4-2d, 5b, 5c and 5d have been discovered. The structures of synthesized compounds were mainly established on the basis of their elemental analysis, $^1H$ NMR, as well as their mass spectral data. All the title compounds were screened for their antifungal activities, and some of the compounds showed promising activity.
Keywords
Halogenopurines; 2-Amino-6-chloropurine; Phase transfer catalyst; Chlorine-exchange halogenation; Diazotization; Fungicidal activity;
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