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Regioselective synthesis and bioactivity of new 5-amino-6-arylamino-pyrazolo[3,4-d]-pyrimidin-4(5H)-one derivatives

✍ Scribed by Hong-Qing Wang; Wei-Ping Zhou; Yu-Yuan Wang; Can-Rong Lin; Zhao-Jie Liu

Publisher
Journal of Heterocyclic Chemistry
Year
2009
Tongue
English
Weight
124 KB
Volume
46
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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A novel approach to regioselective synthesis of new 5‐amino‐6‐arylamino‐1__H__‐pyrazolo[3,4‐d]pyrimidin‐4(5__H__)‐one 5 derivatives via a tandem aza‐wittig and annulation reaction of iminophosphorance 2, aromatic isocyanates and hydrazine in 69.6–94.7% isolated yields is reported. The compound 5 reacted with triethyl orthoformate to give compound 6 in good yield (65.8–82.8%). Their structure was clearly confirmed by spectroscopy data (IR, ^1^H NMR, MS, elemental analysis) and the results of preliminary bioassay indicated that compounds 5 and 6 possess high antifungal activity against Botrytis cinerea Pers and Sclerotinia sclerotiorum, and compound 5h showed 100, 96.4, and 90.2% inhibitory rate to Botrytis cinerea Pers, Pyricularia oryzae, and Sclerotinia sclerotiorum at the concentration of 50 mg/L. The antifungal activities of compound 6 were generally higher than those of compound 5. J. Heterocyclic Chem., (2009).

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