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KMID : 1059520100540040429
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Journal of the Korean Chemical Society
2010 Volume.54 No. 4 p.429 ~ p.436
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Synthesis of Some Biologically Active Halogenopurines
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Hu Yu-Lin
Liu, Xiang
Lu, Ming
Ge, Qiang
Liu, Xiao Bin
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Abstract
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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 POCl₃ 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.
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KEYWORD
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Halogenopurines, 2-Amino-6-chloropurine, Phase transfer catalyst, Chlorine-exchange halogenation, Diazotization, Fungicidal activity
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